Sodium Carbonate → HCID 89813788, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-5-bromopyridine (commercially available from Sigma-Aldrich, Milwaukee, Wis.)(0.114 mL, 5.09 mmol), sodium carbonate (5.09 mL, 10.17 mmol), (S)-5,5-dimethyl-4-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazolidin-2-one (Intermediate J)(2.0 g, 5.09 mmol), and dichloro(1,1-bis(diphenylphosphinoferrocene))palladium(II) (415 mg, 0.509 mmol) were combined in dioxane (10.200 mL) and stirred at 115° C. overnight. LC-MS indicated good conversion to desired product. After cooling to room temperature, the reaction mixture was absorbed 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 100% EtOAc in hexane, to provide (S)-3-(4-(6-aminopyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (1 g, 2.78 mmol, 54.7% yield) as an off-white solid. m/z (ESI) 360.0 (M+H)+.

Provenance & Evidence