Sodium Carbonate → (4S)-5,5-dimethyl-3-(4-(2-oxo-1,2-dihydro-1,7-naphthyridin-3-yl)cyclohex-3-en-1-yl)-4-phenyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with (4S)-5,5-dimethyl-4-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)oxazolidin-2-one (0.124 g, 0.312 mmol), 3-bromo-1,7-naphthyridin-2(1H)-one (0.105 g, 0.468 mmol), sodium carbonate (0.099 g, 0.936 mmol), dioxane (3.0 mL), and water (0.600 mL). Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.026 g, 0.031 mmol) was added, the system was purged with argon, and the tube was sealed. The mixture stirred at 100° C. in the microwave for 1.5 h. The reaction mixture was filtered through Celite® brand filter aid and the filtrate was concentrated to afford a brown oil. This oil was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-10% methanol-ethyl acetate) to afford (4S)-5,5-dimethyl-3-(4-(2-oxo-1,2-dihydro-1,7-naphthyridin-3-yl)cyclohex-3-en-1-yl)-4-phenyloxazolidin-2-one (0.050 g, 38.6% yield) as an off-white solid.

Provenance & Evidence