Potassium Carbonate → HCID 90412716, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-bromo-1-(4-methylphenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (100 g, 284.7 mmol) and (5-fluoro-2-methoxyphenyl)boronic acid (58.05 g, 341.6 mmol) in dimethoxyethane (1600 mL) and water (440 mL) was added potassium carbonate (106.2 g, 768.6 mmol). The mixture was purged with nitrogen and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane adduct (13.95 g, 17.08 mmol) was added. The mixture was purged with nitrogen for 10 minutes and stirred at 100° C. for 1 hour. After concentration, the residue was diluted with ethyl acetate (1500 mL) and washed with aqueous sodium bicarbonate (twice) and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 30-60% ethyl acetate in petroleum ether to afford the title compound.

Provenance & Evidence