Dichloromethane → 4-(4-Bromophenyl)-5-chloro-2-(2-cyano-acetylamino)-thiophene-3-carboxylic acid ethyl ester

Participants

Reaction Steps

To a cold (0° C.) solution of 2-amino-4-(4-bromophenyl)-thiophene-3-carboxylic acid ethyl ester (1.0 g, 3.1 mmol) and triethylamine (0.64 mL, 4.60 mmol) in methylene chloride (6 mL) was added cyanoacetic acid chloride (6.82 mL, 3.41 mmol, 0.5 M in methylene chloride). The cold bath was removed, and the reaction was stirred for 2 h. Saturated aqueous sodium bicarbonate solution (5 mL) was added to the reaction at room temperature. The layers were separated, and the aqueous was extracted with additional methylene chloride (3×5 mL). The combined organic layers were dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide the titled compound as a yellow solid. MS (ESI) m/e 393 (M−H)−, NMR (300 MHz, CDCl3): δ ppm 12.0 (br s, 1H), 7.47 d, 2H), 7.16 (d, 2H), 6.68 (s, 1H), 4.16 (q, 2H), 3.69 (s, 2H), and 100 (t, 3H).

Provenance & Evidence