1-Bromo-4-fluorobenzene → HCID 44177734, compound

Participants

Reaction Steps

A mixture containing 0.035 g (0.08 mmol) of (+/−)-4-chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,5,6,7,8,9-hexahydro-1,4a,7-triaza-benzocyclohepten-9-yl)-benzamide, 0.016 g (0.09 mmol) of 4-bromofluorobenzene, 0.009 g (0.10 mmol) of sodium tert-butoxide, 0.006 g (0.03 mmol) of tri-tert-butylphosphine and 0.007 g (0.01 mmol) of tris(dibenzylideneacetone)dipalladium(0) in 1.60 mL of anhydrous toluene under argon atmosphere was stirred under reflux for 4 h30. The reaction mixture was cooled, aqueous 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 90/10/1 to afford 0.016 g (38%) of the pure product as a powder.

Provenance & Evidence