Potassium Carbonate → HCID 68687850, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 10-(4-iodo-3-methylbenzoyl)-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 74 (0.300 g, 0.53 mmol), phenylboronic acid (0.098 g, 0.80 mmol) and potassium carbonate (0.221 g, 1.60 mmol) in dimethoxyethane:water (8 mL:2 mL) was purged with nitrogen for 10 minutes. [1,1′-bis(Diphenylphosphino)ferrocene]dichloropalladium[II] (0.022 g, 0.0266 mmol) was then added and the reaction mixture heated to 100° C. for 4 hours. The cooled reaction mixture was then partitioned between ethyl acetate (100 mL) and 1 M sodium hydroxide (100 mL). The organic phase was separated, washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give an olive syrup (0.32 g). Purification by flash chromatography using ethyl acetate as solvent afforded the title compound (0.260 g, 95%) as a white foam, m.p. 108-112° C.

Provenance & Evidence