反应详情

Ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate (Example 182, 140 mg, 0.351 mmol) was stirred over Lindlar catalyst (28 mg) in ethanol (15 mL) under 1 atmosphere of hydrogen for 1 hour. The mixture was filtered through Celite with an excess of ethanol. The filtrate was concentrated, and the resulting crude oil was purified by flash chromatography on silica gel eluted with 20% Et2O/hexane. The title compound was collected as a yellow oil (95 mg, 67%). The product had: 1H NMR (300 MHz, acetone-d6) δ 7.78 (d, 1 H), 7.56-7.45 (m, 4 H), 7.34-7.32 (m, 1 H), 7.28-7.26 (m, 1 H), 7.16-7.13 (m, 1 H), 5.93 (s, 2 H), 4.32 (q, 2 H), 3.08 (d, 2 H), 1.31 (t, 3 H), 1.13-1.15 (m, 1 H), 0.42-0.38 (m, 2 H), 0.29-0.26 (m, 2 H).

1. filtrationThe mixture was filtered through Celite with an excess of ethanol
2. concentrationThe filtrate was concentrated
3. customthe resulting crude oil was purified by flash chromatography on silica gel
4. washeluted with 20% Et2O/hexane
5. customThe title compound was collected as a yellow oil (95 mg, 67%)