Sodium Carbonate → HCID 10143682, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 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, Step C (0.200 g, 0.356 mmol), and 2-methoxyphenylboronic acid (0.081 g, 0.533 mmol) in acetonitrile (3 mL) was added a 0.4 M aqueous sodium carbonate solution (3 mL) and the mixture purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.021 g, 0.018 mmol) was then added and the reaction mixture heated to 90° C. for 4 hours. The cooled reaction mixture was partitioned between ethyl acetate (50 mL) and 2 M sodium hydroxide (50 mL). The organic phase was separated, washed with 2 M sodium hydroxide (50 mL), water (50 mL) and brine (50 mL), dried over amnhydrous magnesium sulfate, and concentrated in vacuo to give a yellow syrup (0.23 g). Purification by flash chromatography using a solvent gradient of 1 to 5% methanol in dichloromethane gave a colorless glass that was recrystallized from dichloromethane/hexane to afford the title compound (0.181 g, 94%) as a white solid, m.p. 119-124° C.

Provenance & Evidence