Potassium Phosphate, Tribasic → 5-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole

Participants

Reaction Steps

A solution of benzyl 3-bromobiphenyl-4-yl ether (500 mg, 1.47 mmol) and (1-methyl-1H-pyrazol-5-yl)boronic acid (185 mg, 1.47 mmol) in dioxane (4 mL) was degassed with argon for 30 minutes. Tris(dibenzylideneacetone)dipalladium (0) (54 mg, 0.06 mmol) and tricyclohexylphosphine (33 mg, 0.12 mmol) were added to the mixture under an argon atmosphere. A degassed solution of tripotassium phosphate (626 mg, 2.95 mmol) in water (2 mL) was added and the mixture was stirred at reflux for 16 hours under an argon atmosphere. The cooled reaction mixture was filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was dissolved in ethyl acetate (25 mL) and the solution was washed with water (2×10 mL), brine (10 mL), dried over Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate in hexane) to afforded the title compound (320 mg).

Provenance & Evidence