Trifluoroacetic acid → HCID 57908499, compound

Participants

Reaction Steps

To a solution of commercially available methyl 1H-indole-4-carboxylate (5 g, 28.5 mmol) in 100 mL dichloromethane, at 0° C., was added 3-chlorobenzaldehyde (5 mL, 43.8 mmol), triethylsilane (15 mL, 93.9 mmol) and trifluoroacetic acid (5 mL, 64.9 mmol), and the resulting solution was stirred for ON as it warmed to rt. The reaction was then quenched with saturated aqueous sodium bicarbonate and the solution was extracted with dichloromethane. The organic phases were then combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resultant solid was washed with cold 10:1 hexanes:dichloromethane to yield 6 g of the title compound as a white solid. 1H NMR (500 MHz, d6-acetone): δ 8.5 (s, 1H), 8.0 (m, 2H), 7.4-7.1 (m, 5H), 5.7 (s, 2H), 4.0 (s, 3H).

Provenance & Evidence