Sodium Carbonate → 3-((R)-4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with a mixture of (4R)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohex-1-en-1-yl trifluoromethanesulfonate and (4S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohex-1-en-1-yl trifluoromethanesulfonate (Intermediate M) (730 mg, 1.741 mmol), 2-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)pyrimidine (Intermediate H) (577 mg, 1.915 mmol), sodium carbonate (2 M, 2.611 mL, 5.22 mmol), and tetrakis(triphenylphosphine)palladium(0) (201 mg, 0.174 mmol) (commercially available from Strem Chemicals Inc., Newburyport, Mass.). Dioxane (8.703 mL) was added, the system was purged with argon, and the tube was sealed. The mixture was then stirred at 100° C. in the microwave for 1 hour. LC-MS indicated clean and good conversion to the desired product. The reaction mixture was filtered through Celite® brand filter aid and the filtrate was concentrated to afford a yellow oil. The oil was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0 to 60% EtOAc-heptane) to afford a mixture of 3-((S)-4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one and 3-((R)-4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one (370 mg, 0.832 mmol, 47.8% yield) as a white solid. m/z (ESI) 445.2 (M+H)+.

Provenance & Evidence