Sodium Carbonate → HCID 44178192, compound

Participants

Reaction Conditions

Reaction Steps

A mixture containing 0.145 g (0.28 mmol) of 9-(4-bromo-benzoylamino)-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester (example 10), 0.082 g (0.40 mmol) of 1-methyl-1H-pyrazole-4-boronic acid pinacol ester, 0.35 mL (0.71 mmol) of sodium carbonate (solution 2M), 0.065 g (0.06 mmol) of tetrakis(tri-phenylphosphine)palladium in 5.60 mL of toluene/EtOH (10/1) under argon atmosphere was stirred at 90° C. for 15 hours. The reaction mixture was cooled, aqueous saturated solution of sodium carbonate was added and the resulting solution extracted with dichloromethane. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 98/2/0.2 to 97/3/0.3 to afford 0.088 g (76%) of the pure product as a white powder.

Provenance & Evidence