To a solution of 2-(5-(4-bromophenyl)-1-(2-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)propan-2-ol (115 mg, 0.27 mmol) and 3-(methylsulfonyl)phenylboronic acid (66 mg, 033 mmol) in 1,2-dimethoxyethane (1.5 mL) was added K2CO3 (110 mg, 0.80 mmol) and H2O (1.5 mL). The resulting biphasic suspension was stirred at ambient temperature and sparged with nitrogen for 10 minutes. The reaction was then treated with dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (11) dichloromethane adduct (15 mg, 18 μmol) and heated to 80° C. in an oil bath. The reaction was heated at 80° C. for three hours and then allowed to cool to ambient temperature overnight. The cooled reaction mixture was diluted with EtOAc and H2O. The aqueous layer was extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to afford crude product as a dark oil. The crude product was purified by flash-column chromatography eluting with a gradient from 10% to 100% EtOAc/hexane to afford 2-(5-(3′-(methylsulfonyl)biphenyl-4-yl)-1-(2-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)propan-2-ol (122 mg, 90% yield) as an off-white powder. MS(ES): 501 [M+H]+.
