Potassium Carbonate → 10-[(2'-Methoxy-1,1'-biphenyl-4-yl)sulfonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 10-[(4-bromophenyl)sulfonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Step C (0.500 g, 0.93 mmol), 2-methoxyphenylboronic acid (0.212 g, 1.40 mmol) and potassium carbonate (0.386 g, 2.79 mmol) in dimethoxyethane:water (8 mL:2 mL) was purged with nitrogen for 10 minutes. [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium[II] (38 mg, 0.0465 mmol) was then added and the reaction mixture heated to 90° C. for 21 hours. The cooled reaction mixture was partitioned between ethyl acetate (100 mL) and 1 M sodium hydroxide (100 mL). The separated organic phase was washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a brown syrup (0.60 g). Purification by flash chromatography using a solvent gradient of 0 to 3% methanol in dichloromethane gave the title compound (0.520 g, 99%) as a yellow foam.

Provenance & Evidence