Potassium Carbonate → HCID 90009140, 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, 263 mg, 0.548 mmol) in THF (3.0 mL) was added 5-chloro-2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (221 mg, 0.821 mmol), 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (17.8 mg, 0.027 mmol), and aqueous potassium carbonate (0.821 mL, 2.0 M). The mixture was degassed, flushed with nitrogen and heated to 40° C. for 18 hours. The reaction was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography to afford (4S,5R)-3-{[5-(5-chloro-2-methoxypyridin-3-yl)-2-(methylsulfanyl)pyrimidin-4-yl]methyl}-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (211 mg, 0.389 mmol). LCMS (M+H)+: 543.0.

Provenance & Evidence