Potassium Carbonate → (4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-(5-chloro-2-methoxypyridin-3-yl)-2-(3-fluoroazetidin-1-yl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

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(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(3-fluoroazetidin-1-yl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 14, 425 mg, 0.763 mmol), 5-chloro-2-methoxypyridin-3-ylboronic acid (214 mg, 1.144 mmol), 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (49.7 mg, 0.076 mmol) and K2CO3 (316 mg, 2.288 mmol) were added to a reaction vial that was evacuated and charged with nitrogen three times. The solid reactants were then mixed with THF (4 mL) and water (400 μl), degassed and refilled with nitrogen, capped and heated for 30 minutes at 125° C. in a BIOTAGE microwave reactor, after which LCMS showed complete conversion to product. The reaction was diluted with 5 mL acetonitrile and filtered through a 1 g RP C18 silica cartridge, eluting with 15 mL acetonitrile until filtrate was colorless. The filtrate was concentrated prior to RP Prep purification on a X-Bridge 30×300 mm RP column. The sample was loaded in 7:3:1 CH3CN/water/DMSO (5 mL) and eluted with a 10-100% acetonitrile/water (0.1% NH4OH) linear gradient over 20 minutes. The product of interest eluted in 80% portion of above gradient. Pure fractions (rich cut; impure discarded) were concentrated and lyophilized to give a white solid. LCMS (M+H)+: 619.1. 1H NMR (CDCl3, 500 MHz): δ 8.24 (s, 1H) 8.16 (s, 1H) 7.93 (s, 1H) 7.77 (s, 2H) 7.53 (s, 1H) 5.73 (m, 1H) 5.57 (m, 0.5H) 5.46 (m, 0.5H), 4.70 (d, J=17.4 Hz, 1H), 4.48 (m, 4H), 4.06 (d, J=17.5 Hz, 1H), 3.97 (s, 3H), 0.78 (bs, 3H). Rotomers gave broad signals. SPA IC50: 38 nM.

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