Phenylboronic Acid → 1,1,1-Trifluoro-4-(4-methoxybiphenyl-3-yl)4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol

Participants

Reaction Steps

A mixture of 4-(5-bromo-2-methoxyphenyl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol (188 mg, 0.4 mmol), Pd(OAc)2 (9 mg, 0.04 mmol), DCyBPP ((2-dicyclohexylphosphino)biphenyl, 28 mg, 0.08 mmol), and KF (93 mg, 1.6 mmol) in 3 mL of THF at room temperature was treated with phenylboronic acid (74 mg, 0.6 mmol). The reaction mixture was microwaved for 20 minutes at 120° C., cooled to room temperature, diluted with 20 mL of ethyl acetate and filtered through diatomaceous earth. The filtrate was washed with 5 mL of 1.0 M aqueous sodium hydroxide solution, water, and 5 mL of brine. The organic phase was dried over magnesium sulfate, filtered, and the solvent evaporated in vacuo. The residue was purified silica gel chromatography to provide 75 mg (40% yield) of the title compound as a white solid.

Provenance & Evidence