Potassium Carbonate → HCID 118021393, compound

Participants

Reaction Conditions

Reaction Steps

(4S,5R)-3-{[5-Bromo-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-5-[3-(trifluoromethoxy)phenyl]-1,3-oxazolidin-2-one (INTERMEDIATE 9, 345 mg, 0.721 mmol), 5-chloro-2-methoxypyridin-3-ylboronic acid (203 mg, 1.082 mmol) and K2CO3 (299 mg, 2.164 mmol) were added to a round bottom flask, which was then evacuated and charged with nitrogen 3 times. THF (4 mL) and water (0.4 mL) were then added. After evacuating and charging again with nitrogen, 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (47.0 mg, 0.072 mmol) was added and the reaction heated for 60 minutes at 85° C. LCMS showed complete conversion to product. The reaction was diluted with 5 mL acetonitrile and filtered through a 1 g C18 cartridge, eluting with 15 mL acetonitrile until the filtrate was colorless. The filtrate was then concentrated. Silica gel chromatography using a 0-30% ethyl acetate/hexanes linear gradient followed by an isocratic hold of 30% ethyl acetate/hexanes gave the title compound as a colorless oil. LCMS (M+H)+: 541.2.

Provenance & Evidence