2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of. Indoles
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1 2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles Takumi Abe*, Takuro Suzuki, Masahiro Anada, Shigeki Matsunaga, and Koji Yamada* Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-tobetsu, Hokkaido , Japan Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo , Japan abe-t@hoku-iryo-u.ac.jp kyamada@hoku-iryo-u.ac.jp SUPPORTING INFORMATION Contents 1. General Experimental S2 2. Experimental Procedure S References S17 4. Copies of 1 H, 13 C -NMR spectra s
2 Experimental Section 1. General Experimental Melting points were recorded with a Yanaco MP3 and are uncorrected. High-resolution MS spectra were recorded with a JEOL JMS-T100LP mass spectrometers. IR spectra were measured with a Shimadzu IRAffinity-1 spectrometer. The NMR experiments were performed with a JEOL JNM-ECA500 (500 MHz) spectrometer, and chemical shifts are expressed in ppm ( ) using residual undeuterated solvent as an internal reference (CDCl3 1 H-NMR 7.25, 13 C-NMR 77.1; DMSO 1 H-NMR 2.47, 13 C-NMR 40.0, CD3OD 1 H-NMR 3.29, 13 C-NMR 47.7). The following abbreviations were used to explain NMR peak multiplicities: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broad. Flash column chromatography was performed on silica gel (Silica Gel 60N, Kanto Chemical Co., Ltd.) or activated alumina (Aluminium oxide 90 active neutral, Merck KGaA). 2. Experimental Procedure trans-3-bromo-2-hydroxy-1-tosylindoline (2) To a solution of 1 (1.36 g, 5.0 mmol) and H2O (0.9 ml, 50 mmol) in acetone (50 ml) was added NBS (0.98 g, 5.5 mmol). The mixture was stirred at room temperature until the complete disappearance of starting material as indicated by TLC. After evaporation, the residue was purified by silica gel column chromatography (AcOEt hexane, 1:3) to give 2 (1.56 g, 85% yield) g, 85% yield. colorless viscous oil; IR (CHCl3): 3568, 3480, 1601 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.76 (d, J = 8.0 Hz, 2H), 7.56 (d, J = 8.6 Hz, 1H), 7.30 (t, J = 6.9 Hz, 1H), 7.29 (d, J = 6.9 Hz, 1H), 7.23 (d, J = 8.0 Hz, 2H), 7.07 (t, J = 7.7 Hz, 1H), 6.00 (s, 1H), 5.07 (s, 1H), 2.34 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 144.8, 140.0, 135.2, 130.8, 129.9, 129.9, 127.4, 126.6, 124.9, 115.0, 93.7, 48.9, 21.7; HRMS (ESI): calcd for C15H14BrNO3SNa [M+Na] and , found and A trans-configuration was confirmed by comparison with HC2-HC3 coupling constant of trans- and cis-3-hydroxy-2-methoxy-1-tosylindolines reported by Sakamoto et al. 1 2
3 3-Bromo-1-tosylindole (3) 2 Compound 2 (180 mg, 0.46 mmol) was preserved at room temperature for 24 h. The residue was dried under reduced pressure to give 3 (161 mg, quant.). 161 mg, quantitative yield. colorless prisms; mp C (CHCl3-hexane); IR (KBr): 1599 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.99 (d, J = 7.5 Hz, 1H), 7.77 (d, J = 8.0 Hz, 2H), 7.62 (s, 1H), 7.49 (d, J = 8.0 Hz, 1H), 7.37 (t, J = 8.0 Hz, 1H), 7.30 (d, J = 7.5 Hz, 1H), 7.23 (d, J = 8.6 Hz, 2H), 2.34 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 145.5, 134.9, 134.3, 130.1, 129.8, 127.0, 125.8, 124.9, 124.0, 120.1, 113.7, 99.7, 21.7; HRMS (ESI): calcd for C15H13BrNO3S [M+H] and , found and trans-2-hydroxy-1-tosylindoline-3-ammonium bromide (5) To a solution of 1 (3.00 g, 11 mmol) and H2O (1.98 ml, 110 mmol) in acetone (110 ml) was added NBS (2.17 g, 12 mmol). The mixture was stirred at room temperature until the complete disappearance of starting material as indicated by TLC. Et3N (1.69 ml, 12 mmol) was added to the mixture and stirred further 1 h. The resulting precipitate was separated by filtration, washed with acetone, and dried in vacuo to give 5 (3.89 g, 75% yield) g, 75% yield. colorless prisms; mp C (MeOH); IR (KBr): 3163, 1601 cm 1 ; 1H-NMR (500 MHz, DMSO-d6): 8.02 (d, J = 8.0 Hz, 2H), 7.88 (d, J = 6.9 Hz, 1H), 7.55 (d, J = 8.1 Hz, 1H), 7.48 (t, J = 7.5 Hz, 1H), 7.40 (d, J = 8.0 Hz, 2H), 7.37 (d, J = 8.0 Hz, 1H), 7.14 (t, J = 7.5 Hz, 1H), 6.35 (d, J = 7.5 Hz, 1H), 4.82 (s, 1H), (m, 6H), 2.33 (s, 3H), 1.01 (t, J = 7.5 Hz, 9H); 13 C-NMR (125 MHz, DMSO-d6): 145.4, 142.8, 136.1, 132.9, 130.4, 130.4, 128.2, 124.0, 120.4, 113.8, 84.8, 75.4, 53.3, 21.5, 8.8; HRMS (ESI): calcd for C21H29N2O3S [M] , found Stereo configuration of 5 was unambiguously confirmed by X-ray single crystal structure analysis 3 and NOE experiment. 3
4 trans-2-hydroxy-3-phenylamino-1-tosylindoline (6a) A mixture of 5 (94 mg, 0.2 mmol), aniline (0.02 ml, 0.22 mmol) and Et3N (0.06 ml, 0.4 mmol) in AcOEt (4 ml) was heated under reflux with stirring for 1 h. After addition of H2O, the whole was extracted with AcOEt (3 x 10 ml), washed with brine (10 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (AcOEt hexane, 1:5) to give 6a (71 mg, 93% yield). 71 mg, 93% yield. colorless prisms; mp C (MeOH); IR (CHCl3): , 1504 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.56 (d, J = 8.6 Hz, 2H), 7.56 (d, J = 8.6 Hz, 1H), 7.36 (t, J = 8.0 Hz, 1H), 7.30 (d, J = 7.5 Hz, 1H), 7.21 (t, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 7.11 (t, J = 7.5 Hz, 1H), 6.81 (t, J = 7.5 Hz, 1H), 6.55 (d, J = 8.0 Hz, 2H), 5.61 (s, 1H), 4.68 (s, 1H), 3.48 (br s, 1H), 2.38 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 145.4, 144.5, 140.7, 135.1, 130.4, 129.9, 129.9, 129.5, 127.1, 126.2, 124.7, 118.8, 115.4, 113.4, 91.1, 61.5, 21.7; HRMS (ESI): calcd for C21H20N2O3SNa [M+Na] , found A trans-configuration was confirmed by comparison with HC2-HC3 coupling constant 1 and NOE experiment. trans-2,3-di(phenylamino)-1-tosylindoline (6b) A mixture of 5 (94 mg, 0.2 mmol), aniline (0.04 ml, 0.4 mmol) and Et3N (0.06 ml, 0.4 mmol) in DMF (4 ml) was heated at 50 C with stirring for 1 h. After addition of H2O, the whole was extracted with AcOEt (3 x 10 ml), washed with brine (10 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (AcOEt hexane, 1:5) to give 6b (54 mg, 59% yield). 54 mg, 59% yield. colorless needles; mp C (MeOH); IR (CHCl3): 3422, 1603, 1504 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.66 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 8.6 Hz, 2H), 7.40 (d, J = 8.0 Hz, 1H), 7.31 (d, J = 7.5 Hz, 1H), (m, 7H), 6.86 (t, J = 7.5 Hz, 4
5 1H), 6.82 (d, J = 8.0 Hz, 2H), 6.79 (t, J = 6.9 Hz, 1H), 6.44 (d, J = 8.0 Hz, 2H), 5.63 (s, 1H), 4.65 (s, 1H), 2.40 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 145.4, 144.2, 144.1, 141.5, 135.4, 131.2, 130.5, 129.7, 129.6, 129.4, 127.5, 126.4, 125.3, 120.1, 118.7, 117.8, 115.8, 113.5, 79.3, 61.3, 21.7; HRMS (ESI): calcd for C27H26N3O2S [M+H] ; found A trans-configuration was confirmed by comparison with HC2-HC3 coupling constant 1 and NOE experiment. 3-Phenylamino-1-tosylindole (7a) To a solution of of 6a (79 mg, 0.2 mmol) in AcOEt (2 ml) was added BF3 Et2O (0.13 ml, 1.0 mmol), and the mixture was heated at 50 C with stirring for 3 h. After addition of saturated NaHCO3 aq., the whole was extracted with AcOEt (3 x 10 ml), washed with brine (10 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (AcOEt hexane, 1:5) to give 7a (65 mg, 87%). 65 mg, 87%. colorless viscous oil; IR (CHCl3): 3424, 1599 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 8.06 (d, J = 8.0 Hz, 1H), 7.74 (d, J = 8.6 Hz, 2H), 7.42 (s, 1H), 7.39 (d, J = 7.4 Hz, 1H), 7.36 (t, J = 7.4 Hz, 1H), 7.26 (t, J = 8.0 Hz, 2H), 7.22 (t, J = 8.0 Hz, 1H), 7.19 (d, J = 8.0 Hz, 2H), 6.93 (d, J = 7.5 Hz, 2H), 6.90 (t, J = 7.5 Hz, 1H), 2.32 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 144.8, 144.1, 134.9, 134.6, 129.8, 129.5, 127.1, 126.9, 126.3, 125.5, 123.3, 120.2, 118.4, 115.7, 114.5, 112.8, 21.6; HRMS (ESI): calcd for C21H19N2O3S [M+H] , found General Procedure for the Reaction of 5 with Various Amines A mixture of 5 (235 mg, 0.5 mmol), various amines (0.55 mmol) and Et3N (0.14 ml, 1.0 mmol) in AcOEt (5 ml) was heated under reflux with stirring for h. After addition of H2O, the whole was extracted with AcOEt (3 x 15 ml), washed with brine (15 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to give 6 which was dissolved in AcOEt (5 ml). To this solution was added BF3 Et2O (0.31 ml, 2.5 mmol) and the mixture was heated at 50 C with stirring for 3 h. After addition of saturated NaHCO3 aq., the whole was extracted with AcOEt (3 x 15 ml), washed with brine (15 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography 5
6 (AcOEt hexane, 1:10 1:3) to give 7. N-Methyl-3-phenylamino-1-tosylindole (7b) 160 mg, 85% yield. colorless prisms; mp C (MeOH); IR (CHCl3): 1593, 1501 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 8.03 (d, J = 8.6 Hz, 1H), 7.75 (d, J = 8.6 Hz, 2H), 7.33 (s, 1H), 7.29 (t, J = 7.5 Hz, 1H), 7.22 (d, J = 8.6 Hz, 2H), 7.19 (t, J = 7.5 Hz, 2H), 7.07 (t, J = 7.5 Hz, 1H), 6.98 (d, J = 8.1 Hz, 1H), 6.89 (t, J = 7.5 Hz, 1H), 7.80 (t, J = 7.5 Hz, 2H), 3.32 (s, 3H), 2.35 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 148.6, 144.9, 135.0, 134.9, 133.0, 129.9, 129.1, 127.2, 126.9, 125.1, 123.1, 120.6, 120.4, 117.8, 117.2, 114.3, 41.9, 21.7; HRMS (ESI): calcd for C22H21N2O2S [M+H] , found Scale-up reaction (5, 2.35 g, 5 mmol; AcOEt, 50 ml): 1.59 g, 84% yield. 3-(4-Hydroxyphenyl)amino-1-tosylindole (7c) 155 mg, 82% yield. yellow powder; mp C (CHCl3-hexane); IR (CHCl3): 3597, 3420, 1611, 1514 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 8.02 (d, J = 8.0 Hz, 1H), 7.69 (d, J = 8.6 Hz, 2H), 7.36 (d, J = 7.5 Hz, 1H), 7.32 (t, J = 7.5 Hz, 1H), 7.19 (t, J = 7.5 Hz, 1H), 7.14 (d, J = 8.0 Hz, 2H), 6.87 (d, J = 8.6 Hz, 2H), 6.78 (d, J = 8.6 Hz, 2H), 2.28 (s, 3H); 13C-NMR (125 MHz, CDCl3): 150.3, 144.8, 137.1, 134.8, 134.6, 129.8, 128.6, 126.8, 126.7, 125.6, 123.3, 118.8, 118.2, 116.4, 114.5, 109.8, 21.6; HRMS (ESI): calcd for C21H19N2O3S [M+H] , found (2-Methoxycarbonylphenyl)amino-1-tosylindole (7d) 172 mg, 82% yield. colorless prisms; mp C (MeOH); IR (CHCl3): 3316, 1682, 6
7 1597 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 9.68 (br s, 1H), 8.05 (d, J = 8.6 Hz, 1H), 8.00 (dd, J = 8.6, 1.7 Hz, 1H), 7.75 (d, J = 8.6 Hz, 2H), 7.52 (s, 1H), 7.48 (d, J = 8.0 Hz, 1H), (m, 2H), 7.24 (t, J = 7.5 Hz, 1H), 7.20 (d, J = 8.0 Hz, 2H), 7.03 (d, J = 8.6 Hz, 1H), 6.77 (t, J = 8.0 Hz, 1H), 3.92 (s, 3H), 2.32 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 169.2, 147.9, 145.0, 134.9, 134.7, 134.4, 131.7, 129.9, 127.5, 126.9, 125.6, 124.4, 123.4, 118.9, 117.4, 115.0, 114.4, 114.3, 111.8, 52.0, 21.6; HRMS (ESI): calcd for C23H20N2O4SNa [M+Na] , found (2-Methoxycarbonylphenyl-N-methyl)amino-1-tosylindole (7e) 95 mg, 44% yield. pale yellow powder; mp C (MeOH); IR (CHCl3): 1724, 1595 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.98 (d, J = 8.6 Hz, 1H), 7.75 (d, J = 8.6 Hz, 1H), 7.75 (d, J = 8.6 Hz, 2H), 7.35 (dt, J = 8.0, 1.7 Hz, 1H), (m, 4H), 7.10 (s, 1H), 7.01 (d, J = 8.0 Hz, 1H), 6.95 (t, J = 8.0 Hz, 1H), 6.57 (d, J = 8.6 Hz, 1H), 3.56 (s, 3H), 3.25 (s, 3H), 2.33 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 167.5, 148.4, 144.7, 135.2, 134.9, 134.7, 132.6, 131.2, 129.8, 127.3, 127.0, 126.0, 125.8, 124.9, 124.4, 122.8, 120.7, 114.0, 110.9, 52.1, 43.5, 21.6; HRMS (ESI): calcd for C24H23N2O4S [M+H] , found Allylamino-1-tosylindole (7f) 42 mg, 26% yield. pale yellow viscous oil; IR (CHCl3): 1611 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 8.01 (d, J = 8.6 Hz, 1H), 7.66 (d, J = 8.6 Hz, 2H), (m, 2H), 7.20 (t, J = 8.0 Hz, 1H), 7.13 (d, J = 8.1 Hz, 2H), 6.71 (s, 1H), (m, 1H), 5.31 (dq, J = 17.8, 1.7 Hz, 1H), 5.21 (dt, J = 10.3, 1.7 Hz, 1H), 3.75 (dt, J = 5.2, 1.7 Hz, 2H), 2.29 (s, 3H); 13C-NMR (125 MHz, CDCl3): 144.4, 135.2, 134.7, 134.6, 133.5, 129.6, 126.8, 126.0, 125.4, 123.1, 117.5, 116.9, 114.7, 104.7, 48.6, 21.6; HRMS (ESI): calcd for C18H19N2O2S [M+H] , found
8 3-tert-Butylamino-1-tosylindole (7g) 91 mg, 53% yield. pale yellow powder; mp C (MeOH); IR (CHCl3): 1611 cm 1 ; 1H-NMR (500 MHz, CDCl3): 8.01 (d, J = 8.6 Hz, 1H), 7.66 (d, J = 8.6 Hz, 2H), 7.30 (t, J = 8.0 Hz, 1H), 7.28 (d, J = 8.0 Hz, 1H), 7.19 (t, J = 8.0 Hz, 1H), 7.12 (d, J = 8.6 Hz, 2H), 6.85 (s, 1H), 2.29 (s, 3H), 1.33 (s, 9H); 13 C-NMR (125 MHz, CDCl3): 144.4, 134.6, 134.6, 129.8, 129.5, 128.0, 126.8, 125.2, 123.0, 117.4, 114.7, 107.3, 51.7, 29.1, 21.6; HRMS (ESI): calcd for C19H23N2O2S [M+H] , found Diethylamino-1-tosylindole (7h) 142 mg, 83% yield. colorless powder; mp C (MeOH); IR (CHCl3): 1589 cm 1 ; 1H-NMR (500 MHz, CDCl3): 8.02 (d, J = 8.6 Hz, 1H), 7.67 (d, J = 8.6 Hz, 2H), 7.51 (d, J = 8.0 Hz, 1H), 7.29 (t, J = 8.0 Hz, 1H), 7.19 (t, J = 7.5 Hz, 1H), 7.14 (d, J = 8.6 Hz, 2H), 6.90 (s, 1H), 3.18 (q, J = 7.5 Hz, 4H), 2.29 (s, 3H), 1.07 (t, J = 7.2 Hz, 6H). 13C-NMR (125 MHz, CDCl3): 144.5, 135.6, 135.5, 134.7, 129.6, 127.7, 126.8, 124.9, 123.0, 120.1, 114.5, 111.7, 45.9, 21.6, 11.7; HRMS (ESI): calcd for C19H23N2O2S [M+H] , found Benzylamino-1-tosylindole (7i) 115 mg, 61% yield. colorless powder; mp C (MeOH); IR (CHCl3): 1612 cm 1 ; 1H-NMR (500 MHz, CDCl3): 8.01 (d, J = 8.6 Hz, 1H), 7.55 (d, J = 8.6 Hz, 2H), (m, 7H), 7.20 (t, J = 7.5 Hz, 1H), 7.10 (d, J = 8.6 Hz, 2H), 6.67 (s, 1H), 4.31 (s, 2H), 2.30 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 144.3, 138.5, 135.2, 134.5, 133.5, 129.5, 8
9 128.8, 127.8, 127.6, 126.8, 126.0, 125.4, 123.1, 117.5, 114.8, 104.9, 50.2, 21.6; HRMS (ESI): calcd for C22H21N2O2S [M+H] , found General Procedure for the Reaction of 5 with Various Nucleophiles Method A for 9a 9d: A mixture of 5 (235 mg, 0.5 mmol), phenols (2.5 mmol) and Et3N (0.35 ml, 2.5 mmol) in AcOEt (5 ml) was heated under reflux with stirring for 1 5 h. After addition of H2O, the whole was extracted with AcOEt (3 x 15 ml), washed with brine (15 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to give 8 which was dissolved in AcOEt (5 ml). To this solution was added BF3 Et2O (0.31 ml, 2.5 mmol), and heated at 50 C with stirring for 3 h. After addition of saturated NaHCO3 aq., the whole was extracted with AcOEt (3 x 15 ml), washed with brine (15 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (AcOEt hexane, 1:10 1:3) to give 9a 9d. Method B for 9e 9g: A mixture of 5 (235 mg, 0.5 mmol) and indoles (2.5 mmol) in AcOEt (5 ml) was heated under reflux with stirring for 1 2 h. After addition of H2O, the whole was extracted with AcOEt (3 x 15 ml), washed with brine (15 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to give 8 which was dissolved in AcOEt (5 ml). To this solution was added TsOH H2O (9.5 mg, 0.05 mmol), and heated at reflux with stirring for 2 h. The reaction mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (AcOEt hexane, 1:10 1:3) to give 9 e 9g. Method C for 9h, i: A mixture of 5 (235 mg, 0.5 mmol), diamines (0.55 mmol) and Et3N (0.35 ml, 2.5 mmol) in AcOEt (5 ml) was heated under reflux with stirring for h. After addition of H2O, the whole was extracted with AcOEt (3 x 15 ml), washed with brine (15 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (AcOEt hexane, 1:2) to give 9h and 9i. 3-Phenoxy-1-tosylindole (9a) 9
10 122 mg, 67% yield. colorless prisms; mp C (MeOH); IR (CHCl3): 1589 cm 1 ; 1H-NMR (500 MHz, CDCl3): 8.06 (d, J = 9.1 Hz, 1H), 7.74 (d, J = 8.6 Hz, 2H), (m, 4H), 7.23 (s, 1H), 7.21 (d, J = 8.0 Hz, 2H), 7.19 (t, J = 8.1 Hz, 1H), 7.12 (t, J = 7.5 Hz, 1H), 7.04 (d, J = 8.0 Hz, 2H),2.34 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 157.5, 145.1, 141.6, 134.8, 134.2, 129.9, 129.9, 126.9, 125.7, 124.8, 123.6, 123.5, 119.0, 117.4, 114.3, 112.8, 21.7; HRMS (ESI): calcd for C21H18NO3S [M+H] +, found (2-Methoxycarbonylphenoxy)-1-tosylindole (9b) 82 mg, 39%. colorless prisms; mp C (CHCl3-hexane); IR (CHCl3): 1721, 1601 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 8.03 (d, J = 8.1 Hz, 1H), 7.93 (dd, J = 8.1, 1.7 Hz, 1H), 7.71 (d, J = 8.6 Hz, 2H), 7.41 (t, J = 8.1 Hz, 1H), 7.38 (d, J = 8.0 Hz, 1H), 7.34 (t, J = 8.0 Hz, 1H), (m, 4H), 7.14 (s, 1H), 6.97 (d, J = 8.0 Hz, 1H), 3.73 (s, 3H), 2.34 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 166.1, 156.6, 145.1, 141.9, 134.8, 134.0, 133.8, 132.1, 129.9, 126.9, 125.8, 124.5, 123.7, 123.6, 121.9, 119.0, 118.7, 114.3, 112.5, 52.2, HRMS (ESI): calcd for C23H20NO5S [M+H] +, ; found (2-Formylphenoxy)-1-tosylindole (9c) 94 mg, 48% yield. colorless prisms; mp C (CHCl3-hexane); IR (CHCl3): 1692, 1601 cm 1 ; 1 H-NMR (500 MHz, CDCl3): (s, 1H), 8.06 (d, J = 8.6 Hz, 1H), 7.93 (dd, J = 7.5, 1.7 Hz, 1H), 7.74 (d, J = 8.6 Hz, 2H), 7.48 (ddd, J = 8.6, 7.5, 1.2 Hz, 1H),7.38 (ddd, J = 8.6, 7.5, 1.7 Hz, 1H), 7.34 (d, J = 8.0 Hz, 1H), 7.29 (s, 1H), (m, 4H), 6.90 (d, J = 8.6 Hz, 1H), 2.36 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 188.9, 159.8, 145.3, 140.5, 136.0, 134.7, 134.0, 130.1, 128.8, 127.0, 126.1, 125.9, 124.1, 123.8, 123.7, 118.7, 116.9, 114.4, 113.7, 21.7; HRMS (ESI): calcd for C22H18NO4S: [M+H] +, found
11 3-(Naphthalene-2-yloxy)-1-tosylindole (9d) 64 mg, 31% yield. colorless powder; mp C (CHCl3-hexane); IR (CHCl3): 1597 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 8.09 (d, J = 8.0 Hz, 1H), (m, 2H), 7.75 (d, J = 8.6 Hz, 2H), 7.63 (d, J = 8.0 Hz, 1H), 7.46 (t, J = 8.0 Hz, 1H), 7.41 (t, J = 8.0 Hz, 1H), 7.38 (t, J = 8.1 Hz, 1H), 7.36 (d, J = 8.0 Hz, 1H), 7.31 (dd, J = 8.6, 2.3 Hz, 1H), 7.30 (s, 1H), 7.26 (d, J = 2.3 Hz, 1H), 7.24 (d, J = 8.6 Hz, 2H), 7.18 (t, J = 8.0 Hz, 1H), 2.37 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 155.3, 145.1, 141.4, 134.9, 134.2, 134.2, 130.3, 130.1, 130.0, 127.9, 127.3, 127.0, 126.8, 125.8, 124.9, 124.8, 123.6, 119.1, 118.6, 114.4, 113.3, 112.3, 21.7; HRMS (ESI): calcd for C25H20NO3S [M+H] +, ; found (Indol-3-yl)-1-tosylindole (9e) 158 mg, 82% yield. colorless powder; mp C (CHCl3-hexane); IR (CHCl3): 3476 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 8.33 (br s, 1H), 8.09 (d, J = 8.6 Hz, 1H), (m, 3H), 7.79 (d, J = 8.1 Hz, 1H), 7.72 (d, J = 8.0 Hz, 1H), 7.48 (d, J = 2.9 Hz, 1H), 7.46 (d, J = 8.0 Hz, 1H), 7.36 (t, J = 8.0 Hz, 1H), (m, 2H), (m, 3H), 2.32 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 145.0, 136.4, 135.5, 135.3, 130.5, 130.0, 126.9, 126.3, 124.9, 123.4, 122.9, 122.6, 122.5, 120.9, 120.5, 120.1, 117.4, 114.0, 111.5, 108.9, 21.7; HRMS (ESI): calcd for C23H18N2O2SNa [M+Na] , found Scale-up reaction (5, 2.35 g, 5 mmol; AcOEt, 50 ml): 1.64 g, 85% yield. 11
12 3-(2-Methylindol-3-yl)-1-tosylindole (9f) 188 mg, 94% yield. colorless prisms; mp C (CHCl3-hexane), IR (CHCl3): 3468, 1599 cm 1 ; 1 H-NMR (500 MHz, CDCl3): (m, 2H), 7.85(d, J = 8.6 Hz, 2H), 7.60 (s, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.41 (d, J = 8.0 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.35 (d, J = 8.0 Hz, 1H), (m, 3H), 7.19 (t, J = 8.1 Hz, 1H), 7.09 (t, J = 8.0 Hz, 1H), 2.42 (s, 3H), 2.35 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 145.0, 135.5, 135.4, 135.3, 133.0, 131.3, 130.0, 128.4, 127.0, 124.8, 124.0, 123.3, 121.7, 121.6, 119.9, 119.3, 117.4, 113.9, 110.6, 105.0, 21.7, 12.7; HRMS (ESI): calcd for C24H21N2O2S [M+H] ; found (2,3,4,4aTetrahydro-1H-carbazol-4a-yl)-1-tosylindole (9g) 88 mg, 40%. colorless prisms; mp C (CHCl3-hexane); IR (CHCl3): 1715, 1585 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.89 (d, J = 8.6 Hz, 1H), 7.78 (s, 1H), 7.77 (d, J = 8.6 Hz, 2H), 7.69 (d, J = 8.0 Hz, 1H), 7.30 (td, J = 7.5, 1.2 Hz, 1H), 7.24 (d, J = 8.6 Hz, 2H), 7.18 (t, J = 8.0 Hz, 1H), 7.06 (t, J = 7.5 Hz, 1H), 7.00 (d, J = 7.5 Hz, 1H), 6.92 (t, J = 7.5 Hz, 1H), 6.65 (d, J = 8.0 Hz, 1H), 3.06 (dd, J = 13.7, 2.3 Hz, 1H), 2.89 (br d, J = 12.6 Hz, 1H), 2.35 (s, 3H), 2.26 (td, J = 13.2, 5.8 Hz, 1H), 2.11 (br d, J = 12.6 Hz, 1H), 1.90 (qt, J = 13.8, 3.5 Hz, 1H), 1.79 (br d, J = 13.8 Hz, 1H), 1.53 (qt, J = 13.2, 4.0 Hz, 1H), 1.53 (td, J = 13.8, 4.0 Hz, 1H); 13 C-NMR (125 MHz, CDCl3): 188.4, 154.4, 145.2, 144.9, 130.0, 128.8, 128.2, 126.9, 125.6, 125.1, 124.1, 123.7, 122.3, 120.6, 120.2, 119.7, 113.7, 57.8, 38.5, 30.8, 29.5, 22.2, 21.7; HRMS (ESI): calcd for C27H25N2O2S [M+H] , found
13 cis-5a,6,10b,11-tetrahydro-6-tosylindolo[2,3-b]quinoxaline (9h) 119 mg, 63% yield. yellow powder; mp C (CHCl3-hexane); IR (CHCl3): 3391, 1610 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.67 (d, J = 8.6 Hz, 2H), 7.42 (d, J = 8.6 Hz, 1H), (m, 3H), 7.16 (d, J = 7.4 Hz, 1H), 7.01 (t, J = 7.5 Hz, 1H), (m, 3H), 6.48 (d, J = 8.0 Hz, 1H), 5.67 (dd, J = 7.5, 2.3 Hz, 1H), 5.06 (br s, 1H), 4.86 (d, J = 8.0 Hz, 1H), 3.77 (br s, 1H), 2.36 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 144.4, 140.5, 135.2, 132.9, 131.7, 131.5, 129.9, 129.8, 127.2, 124.3, 124.0, 120.5, 120.4, 115.4, 115.1, 115.0, 75.5, 56.4, 21.6; HRMS (ESI): calcd for C21H20N3O2S [M+H] , found A cis-configuration was confirmed by comparison with HC2-HC3 coupling constant 1 and NOE experiment. cis-5a,6,13,13a-tetrahydro-5-tosylbenzo[g]indolo[2,3-b]quinox aline (9i) 130 mg, 61%. colorless powder; mp C (CHCl3-hexane), IR (CHCl3): 3385, 1601 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.67 (d, J = 8.6 Hz, 2H), (m, 1H), (m, 1H), 7.40 (d, J = 8.6 Hz, 1H), (m, 6H), 7.00 (d, J = 7.5 Hz, 1H), 6.98 (s, 1H) 6.81 (s, 1H), 5.78 (dd, J = 8.0, 1.7 Hz, 1H), 5.33 (br s, 1H), 5.00 (d, J = 8.6 Hz, 1H), 4.14 (br s, 1H), 2.34 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 144.5, 140.4, 135.2, 134.2, 132.7, 131.4, 130.0, 130.0, 130.0, 129.7, 127.1, 126.0, 125.6, 124.4, 124.0, 123.5, 123.3, 114.9, 110.6, 109.7, 75.4, 56.4, 21.6; HRMS (ESI): calcd for C25H22N3O2S [M+H] , found A cis-configuration was confirmed by comparison with HC2-HC3 coupling constant 1 and NOE experiment. General Procedure for the Reaction of 5 with 1,3-Dicarbonyl Compounds Method D for 10, 14, 16 and 17: A mixture of 5 (235 mg, 0.5 mmol), 1,3-dicarbonyl compounds (2.5 mmol) and Et3N (0.35 ml, 2.5 mmol) in AcOEt (5 ml) was heated under 13
14 reflux with stirring for 2 h. After addition of H2O, the whole was extracted with AcOEt (3 x 15 ml), washed with brine (15 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (AcOEt hexane, 1:5 1:2) to give 10, 14, 16 and 17. Dehydration of 10, 14, 16, 17: To a solution of 10 (14, 16, 17) (0.2 mmol) in AcOEt (2 ml) was added TsOH H2O (3.8 mg, 0.02 mmol), and the mixture was heated at reflux with stirring for 2 h. The reaction mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (AcOEt hexane, 1:5 1:1) to give 11, 15, 18. cis-2,3,3a,8a-tetrahydro-8-tosylfuro[2,3-b]indol-2-one (10) 146 mg, 89%. colorless prisms; mp C (CHCl3-hexane), IR (CHCl3): 1786, 1599 cm 1 ; 1 H-NMR (500 MHz, DMSO-d6): 7.83 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 8.6 Hz, 2H), (m, 3H), 7.07 (td, J = 7.5, 1.2 Hz, 1H), 6.68 (d, J = 6.9 Hz, 1H), (m, 1H), 3.16 (dd, J = 18.3, 9.8 Hz, 1H), 2.71 (dd, J = 18.3, 1.7 Hz, 1H), 2.31 (s, 3H); 13 C-NMR (125 MHz, DMSO-d6): 174.8, 145.4, 139.4, 135.4, 132.3, 130.6, 129.6, 127.9, 126.5, 125.2, 114.0, 94.6, 41.7, 34.2, 21.5; HRMS (ESI): calcd for C17H16NO4S [M+H] , found (1-Tosylindol-3-yl)acetic acid (11) 41 mg, 62% yield. colorless powder; mp C (CHCl3-hexane); IR (CHCl3): 1714 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.97 (d, J = 8.0 Hz, 1H), 7.75 (d, J = 8.6 Hz, 2H), 7.58 (s, 1H), 7.48 (d, J = 7.5 Hz, 1H), 7.32 (t, J = 8.6 Hz, 1H), 7.24 (t, J = 8.1 Hz, 1H), 7.19 (d, J = 8.6 Hz, 2H), 3.72 (s, 2H), 2.31 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 176.6, 145.1, 135.3, 135.0, 130.3, 130.0, 126.9, 125.0, 125.0, 123.4, 119.6, 114.3, 113.8, 30.8, 21.6; HRMS (ESI): calcd for C17H15NO4SNa [M+Na] , found
15 cis-2-acetoxy-3-(2-oxopropyl)-1-tosylindoline (14) 147 mg, 76% yield. colorless prisms; mp C (CHCl3-hexane); IR (CHCl3): 1742, 1599 cm 1, 1 H-NMR (500 MHz, CDCl3): 7.73 (d, J = 8.01 Hz, 2H), 7.58 (d, J = 8.0 Hz, 1H), (m, 3H), 7.03 (t, J = 7.5 Hz, 1H), 6.98 (d, J = 6.9 Hz, 1H), 6.96 (d, J = 7.4 Hz, 1H), 3.80 (q, J = 6.9 Hz, 1H), 2.79 (dd, J = 7.5, 2.8 Hz, 2H), 2.37 (s, 3H), 2.19 (s, 3H), 1.99 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 205.6, 169.2, 144.6, 140.4, 136.0, 131.7, 130.0, 128.6, 127.1, 124.4, 123.8, 114.7, 85.5, 41.5, 40.3, 30.1, 21.7, 20.9; HRMS (ESI): calcd for C20H21NO5SNa [M+Na] , found A cis-configuration was confirmed by comparison with HC2-HC3 coupling constant 1 and NOE experiment. 3-(2-Oxopropyl)-1-tosylindole (15) 52 mg, 80% yield. colorless prisms; mp C (CHCl3-hexane); IR (CHCl3): 1715, 1599 cm 1 ; 1 H-NMR (500 MHz, CDCl3): 7.98 (d, J = 8.0 Hz, 1H), 7.75 (d, J = 8.1 Hz, 2H), 7.54 (s, 1H), 7.40 (d, J = 8.1 Hz, 1H), 7.32 (t, J = 7.5 Hz, 1H), 7.23 (t, J = 7.5 Hz, 1H), 7.20 (d, J = 8.6 Hz, 2H), 3.74 (s, 2H), 2.32 (s, 3H), 2.15 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 205.3, 145.1, 135.2, 135.2, 130.6, 130.0, 126.9, 125.1, 124.9, 123.5, 119.5, 115.5, 113.8, 40.3, 29.2, 21.7; HRMS (ESI): calcd for C18H17NO3SNa [M+Na] , found ,3-b]indol-1-one (16) cis-3,3-dimethyl-6-tosyl-2,3,4,5a,6,10b-hexahydro-1h-benzofuro[ 15
16 A mixture of 5 (235 mg, 0.5 mmol) and dimedone (140 mg, 1.0 mmol) in AcOEt (5 ml) was heated under reflux with stirring for 24 h. After addition of H2O, the whole was extracted with AcOEt (3 x 15 ml), washed with brine (15 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (AcOEt hexane, 2:5) to give 16 (95 mg, 47% yield). 95 mg, 47% yield. colorless powder; mp C (CHCl3-hexane); IR (CHCl3): 1639 cm 1 ; 1 H-NMR (500 MHz, DMSO-d6): 7.80 (d, J = 8.6 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 1H), 7.27 (d, J = 8.0 Hz, 1H), 7.15 (t, J = 7.5 Hz, 1H), 7.05 (d, J = 8.6 Hz, 1H), 6.95 (t, J = 7.5 Hz, 1H), 4.74 (d, J = 8.6 Hz, 1H), 2.37 (d, J = 1.2 Hz, 2H), 2.31 (s, 3H), 2.10 (s, 2H), 0.99 (s, 3H), 0.85 (s, 3H); 13 C-NMR (125 MHz, DMSO-d6): 193.7, 175.7, 145.4, 139.2, 134.9, 132.0, 130.6, 128.8, 127.9, 126.5, 124.8, 113.9, 113.5, 100.1, 50.9, 46.4, 36.8, 34.4, 28.5, 28.1, 21.5; HRMS (ESI): calcd for C23H24NO4S [M+H] , found (2-Hydroxy-4,4-dimethyl-6-oxocyclohexenyl)-1-tosylindole (17) To a solution of 16 (64 mg, 0.2 mmol) in AcOEt (2 ml) was added TsOH H2O (3.5 mg, 0.02 mmol), and the mixture was heated at reflux with stirring for 1 h. The reaction mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (AcOEt hexane, 2:5) to give 17 (47 mg, 73% yield). 47 mg, 73% yield. colorless powder; mp C (CHCl3-hexane); IR (CHCl3): 3482, 1630 cm 1 ; 1 H-NMR (500 MHz, CD3OD): 7.99 (d, J = 8.6 Hz, 1H), 7.81 (d, J = 8.6 Hz, 2H), 7.59 (s, 1H), (m, 1H), (m, 4H), 2.47 (s, 4H), 2.26 (s, 3H), 1.16 (s, 6H), 13 C-NMR (125 MHz, CD3OD): 186.6, 145.1, 135.2, 134.8, 131.1, 129.6, 126.7, 126.3, 123.8, 122.5, 121.1, 114.1, 113.1, 107.1, 46.7, 31.5, 27.2, 20.1; HRMS (ESI): calcd for C23H24NO4S [M+H] , found Formyl-3-{methyl(phenyl)amino}-1-tosylindole (18) Phosphoryl chloride (0.2 ml, 2 mmol) was added to DMF (1 ml) at 16 C and stirred 16
17 for 0.5 h. A solution of 7b (376 mg, 1 mmol) in DMF (1 ml) was added to the mixture and stirred at room temperature for 1 h. The resultant mixture was added to saturated NaHCO3 aq. (5 ml) at 0 C, and the whole was extracted with AcOEt (3 x 10 ml), washed with saturated NaHCO3 aq. (10 ml). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (AcOEt hexane, 1:5) to give 18 (341 mg, 84% yield). 341 mg, 84% yield. yellow powder; mp C (MeOH); IR (CHCl3): 1665, 1599 cm 1 ; 1 H-NMR (500 MHz, CDCl3): (s, 1H), 8.25 (d, J = 8.6 Hz, 1H), 7.50 (d, J = 8.6 Hz, 2H), 7.45 (ddd, J = 8.6, 7.5, 1.2 Hz, 1H), 7.19 (dd, J = 8.6, 7.5 Hz, 2H), 7.12 (d, J = 8.6 Hz, 2H), 7.03 (ddd, J = 8.6, 7.5, 1.2 Hz, 1H), 6.95 (t, J = 7.5 Hz, 1H), 6.80 (d, J = 7.5 Hz, 2H), 6.77 (d, J = 8.1 Hz, 1H), 3.51 (s, 3H), 2.32 (s, 3H); 13 C-NMR (125 MHz, CDCl3): 181.1, 146.1, 145.2, 143.4, 138.6, 133.0, 129.5, 129.4, 129.1, 127.2, 127.0, 127.0, 124.5, 123.4, 122.0, 118.4, 117.0, 43.8, 21.7; HRMS (ESI): calcd for C23H21N2O3S [M+H] , found Cryptolepine (19) 3 To a solution of Me2NH HCl (8.2 mg, 0.1 mmol) in DMF (1 ml) was added 18 (20 mg, 0.05 mmol) and the mixture was heated at 150 C with stirring for 1.5 h. The mixture was cooled to room temperature and added 5% Na2CO3 aq. (5 ml). After stirring at room temperature for 10 min, the resultant mixture was extracted with AcOEt (3 x 10 ml), washed with saturated Na2CO3 aq. (5 ml). The organic layer was dried over Na2CO3 and concentrated in vacuo. The residue was purified by activated alumina column chromatography (CHCl3, 5% MeOH/CHCl3) to give 19 (7.3mg, 62% yield). 7.3mg, 62% yield. purple solid; mp C (MeOH); IR (KBr): 1628 cm 1 ; 1 H-NMR (500 MHz, DMSO-d6): 8.91 (s, 1H), 8.50 (d, J = 9.2 Hz, 1H), 8.47 (d, J = 8.6 Hz, 1H), 8.37 (d, J = 8.0 Hz, 1H), 7.88 (ddd, J = 9.2, 7.2, 2.0 Hz, 1H), 7.67 (t, J = 7.5 Hz, 1H), 7.63 (d, J = 8.6 Hz, 1H), 7.51 (ddd, J = 8.6, 7.4, 1.2 Hz, 1H), 7.02 (ddd, J = 8.6, 7.4, 1.2 Hz, 1H), 4.90 (s, 3H); 13 C-NMR (125 MHz, DMSO-d6): 158.3, 143.2, 139.2, 133.5, 131.3, 130.0, 129.8, 126.4, 125.7, 125.1, 124.7, 118.7, 117.7, 117.1, 114.2, 39.5; HRMS (ESI): calcd for C16H13N2 [M+H] , found References 1) Chien, C.-S.; Suzuki, T.; Kawasaki T.; Sakamoto M. Chem. Pharm. Bull. 1984, 32, ) An, Y.; Wang, Y.; Hu, X. Eur. J. Org. Chem. 2014, ) Jaromír Touˇsek, VanMiert, S.; Pieters, L.; Van Baelen, G.; Hostyn, S.; Maes, B. U. W.; Lemi`ere G.; Dommissec, R.; Marekd, R. Magn. Reson. Chem. 2008, 46,
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