Potassium Carbonate → (4R,5R)-4-(5-ethynyl-2-fluoropyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one

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Reaction Steps

To a 25 mL round bottom flask was added (4R,5R)-4-(2-fluoro-5-((trimethylsilyl)ethynyl)pyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one (77 mg, 0.207 mmol) in MeOH (4 mL). The solution was stirred and potassium carbonate (28.6 mg, 0.207 mmol) was added in one portion and the reaction was allowed to stir for 30 min. The reaction was complete by TLC and LC/MS. The reaction solvent was then evaporated in vacuo and the crude solid was dissolved in dichloromethane and washed with saturated ammonium chloride. The organic layer was separated, dried over sodium sulfate, and evaporated in vacuo to afford (4R,5R)-4-(5-ethynyl-2-fluoropyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one (60 mg, 0.180 mmol, 87% yield) as an off white solid. This material was used as is without purification. 1H-NMR (CDCl3, 400 MHz) δ 8.39 (s, 1H), 8.07 (dd, J=8.0, 2.0, 1H), 7.47-7.42 (m, 1H), 7.19-7.12 (m, 3H), 5.86 (brs, 1H), 5.37 (d, J=4.0, 1H), 5.02 (s, J=4.0, 1H), 3.31 (s, 1H). LC/Mass spec. (Analytical HPLC method 2): RT=1.82 min. Mass=301.19 (MH)+.

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