Sodium Carbonate → (S)-3-(4-(6-Fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

(S)-3-(4-Iodophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (Intermediate C)(2.61 g, 6.64 mmol), sodium carbonate (6.64 mL, 13.28 mmol), 2-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)pyrimidine (Intermediate H) (2 g, 6.64 mmol), and dichloro(1,1-bis(diphenylphosphinoferrocene))palladium(II) (0.542 g, 0.664 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) were combined in dioxane (16.60 mL) and stirred at 110° C. overngight. LC-MS indicated that there was complete conversion to the desired product. The final reaction material was adsorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 50% EtOAc in hexane, to provide (S)-3-(4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one as yellow solid. m/z (ESI) 441.3 (M+H)+.

Provenance & Evidence