Potassium Carbonate → HCID 90009212, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4S,5R)-3-{[5-bromo-2-(methylsulfanyl)pyrimidin-4-yl]methyl}-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 10, 150 mg, 0.312 mmol) in THF (3.0 mL) was added {5-[4-(tert-butoxycarbonyl)-2-methylphenyl]-2-methoxypyridin-3-yl}boronic acid (INTERMEDIATE 32, 129 mg, 0.375 mmol), 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (10.2 mg, 0.016 mmol), and aqueous potassium carbonate (0.468 mL, 2.0 M). The mixture was degassed, flushed with nitrogen and heated to 90° C. for 45 minutes, then allowed to stir at room temperature overnight. The reaction was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and the filtrate concentrated. The crude product was purified by column chromatography to afford tert-butyl 4-{5-[4-({(4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfanyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (192 mg, 0.275 mmol). LCMS (M+H)+: 699.1

Provenance & Evidence