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 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) (DCM adduct) (0.026 g, 0.031 mmol) was added, the system was purged with argon, and the tube was sealed. The mixture was irradiated at 100° C. in the microwave for 1.5 hours. The reaction mixture was then filtered through Celite® brand filter aid and the filtrate was concentrated to afford a brown oil. The oil thus obtained was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-10% MeOH-EtOAc) to afford Example 87 ((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) (50 mg, 39%) as an off-white solid as a mixture of diastereomers. m/z (ESI) 416.4 (M+H)+.

Provenance & Evidence