81.6% |
With (1S)-10-camphorsulfonic acid In methanol; water at 100℃; for 3h; Inert atmosphere; |
6-Methyl-3-(2-nitro-1-(thiophen-2-yl)ethyl)-2-phenyl-1H-indole (ZCZ011).
(24 mg, 0.1 mmol) was added to a suspension of 6-methyl-2-phenyl-1H-indole (100 mg, 0.48 mmol) andtrans-2-(2-nitrovinyl)thiophene (75 mg, 0.48 mmol) in 2.5 mL of the mixture of MeOH and H2O (1:4). Theresulting mixture was stirred at 100oC under argon atmosphere for 3 hours and cooled to room temperature.The Reaction mixture was partitioned between ethyl acetate and water. The organic extract was separatedand washed with saturated sodium bicarbonate aqueous solution, water, and brine. The resultant organiclayer was separated and dried over sodium sulfate. Filtration and concentration provided solid crudeproduct, which was purified by Combi-flash chromatography (EtOAc/Hexane = 0-20%) to yield the desiredproduct ZCZ011 (142 mg, 81.6%) as a pale yellow solid. mp. 139-140. 1H-NMR (300 MHz, CDCl3) δ8.04 (s, 1H), 7.39-7.49 (m, 6H), 7.19 (s, 2H), 6.94-6.97 (m, 3H), 5.47 (t, J = 7.7 Hz, 1H), 5.18 (1H, dd, J =7.4, 12.5 Hz, 1H), 5.06 (dd, J = 8.2, 12.5 Hz, 1H), 2.46 (s, 3H). APCI-MS m/z: 363.1 (M+H)+. |
81.6% |
With (1S)-10-camphorsulfonic acid In methanol; water at 100℃; for 3h; Inert atmosphere; |
6-Methyl-3-(2-nitro-1-(thiophen-2-yl)ethyl)-2-phenyl-1H-indole (ZCZ011).
(24 mg, 0.1 mmol) was added to a suspension of 6-methyl-2-phenyl-1H-indole (100 mg, 0.48 mmol) andtrans-2-(2-nitrovinyl)thiophene (75 mg, 0.48 mmol) in 2.5 mL of the mixture of MeOH and H2O (1:4). Theresulting mixture was stirred at 100oC under argon atmosphere for 3 hours and cooled to room temperature.The Reaction mixture was partitioned between ethyl acetate and water. The organic extract was separatedand washed with saturated sodium bicarbonate aqueous solution, water, and brine. The resultant organiclayer was separated and dried over sodium sulfate. Filtration and concentration provided solid crudeproduct, which was purified by Combi-flash chromatography (EtOAc/Hexane = 0-20%) to yield the desiredproduct ZCZ011 (142 mg, 81.6%) as a pale yellow solid. mp. 139-140. 1H-NMR (300 MHz, CDCl3) δ8.04 (s, 1H), 7.39-7.49 (m, 6H), 7.19 (s, 2H), 6.94-6.97 (m, 3H), 5.47 (t, J = 7.7 Hz, 1H), 5.18 (1H, dd, J =7.4, 12.5 Hz, 1H), 5.06 (dd, J = 8.2, 12.5 Hz, 1H), 2.46 (s, 3H). APCI-MS m/z: 363.1 (M+H)+. |