Potassium Carbonate → HCID 68689963, 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), 2-thiopheneboronic acid (0.102 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 90° C. for 4 hours. The cooled reaction mixture was 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, and concentrated in vacuo to give a brown syrup (0.34 g). Purification by flash chromatography using 280:8:1 dichloromethane:ethanol:aqueous ammonia as solvent gave an orange foam that was crystallized from diethyl ether/hexane to afford the title compound (0.168 g, 61%) as a tan solid.

Provenance & Evidence