(4S,5R)-3-{[3-bromo-6-(3,3-difluoroazetidin-1-yl)pyridin-2-yl]methyl}-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (530.8 mg, 1.012 mmol), 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (66.0 mg, 0.101 mmol), potassium carbonate (1.519 ml, 3.04 mmol), methyl trans-4-[4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclohexanecarboxylate (INTERMEDIATE 7) (436 mg, 1.164 mmol) and THF (6 ml) were sealed in a reaction vessel and placed in a 90° C. oil bath for 4 hrs. LCMS indicated complete consumption of the starting material and formation of the desired product. Volatiles were removed under reduced pressure. The resulting pot residue was worked up with brine/ethyl acetate. The combined extracts were dried over Na2SO4, filtered and evaporated to afford a dark mixture. This mixture was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 100 g cartridge). The column was eluted by an ethyl acetate/hexanes mixture (0% to 40%). Related fractions were pooled and evaporated in vacuo to afford a brown solid foam of 507 mg as the titled compound. LCMS calc.=691.25. found=692.49 (M+1)+.
