Potassium Carbonate → 10-[(2'-Methyl-1,1'-biphenyl-3-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Participants

Reaction Conditions

Reaction Steps

A mixture of 10-(3-bromobenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Step A (2.0 g, 5.4 mmol), o-tolylboronic acid (0.8 g, 5.9 mmol) and potassium carbonate (2.4 g, 17.7 mmol) in ethylene glycol dimethyl ether: water (20 mL: 5 mL) was purged with nitrogen for 1 hour. [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium [II] (0.22 g, 0.26 mmol) was added and the reaction mixture heated to 75° C. with vigorous stirring for 16 hours. The cooled reaction mixture was then filtered through Celite and the cake washed with dichloromethane (100 mL). The organic phase was separated, washed with 1 M sodium hydroxide (100 mL) and brine (100 mL), dried over anhydrous potassium carbonate and concentrated in vacuo to give the crude product (2.3 g) as a dark brown solid. Purification by flash chromatography using a solvent gradient of 40% to 100% dichloromethane in hexane afforded the title compound (1.7 g, 85%) as a white solid.

Provenance & Evidence