Benzoyl chloride, 3-bromo- → 10-(3-Bromobenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Participants

Reaction Steps

To a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (5.0 g, 27 mmol) and N,N-diisopropylethylamine (7.5 mL, 43 mmol) in dry dichloromethane (135 mL) was added 3-bromobenzoyl chloride (2.9 mL, 22 mmol) and the reaction mixture was stirred at room temperature under nitrogen for 16 hours. The reaction mixture was then washed with 1 M hydrochloric acid (5×200 mL), 1 M sodium hydroxide (200 mL), and brine (200 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a yellow solid (7.2 g). Recrystallization from ethyl acetate gave the title compound (5.8 g, 72%) as a white crystalline solid.

Provenance & Evidence