Sodium Carbonate → HCID 89815624, compound

Participants

Reaction Steps

A microwave vial was charged with (S)-5,5-dimethyl-4-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazolidin-2-one (0.100 g, 0.254 mmol), 3-bromo-1,7-naphthyridin-2(1H)-one (0.063 g, 0.280 mmol), sodium carbonate (0.081 g, 0.763 mmol), dioxane (2.0 mL), and water (0.400 mL). Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) (DCM adduct) (0.021 g, 0.025 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 hour. 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 88 ((S)-5,5-dimethyl-3-(4-(2-oxo-1,2-dihydro-1,7-naphthyridin-3-yl)phenyl)-4-phenyloxazolidin-2-one) (0.020 g, 0.049 mmol, 19.12% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (br. s., 3H), 1.65 (br. s., 3H), 5.52 (br. s., 1H), 7.09-7.49 (m, 5H), 7.49-7.93 (m, 5H), 8.08 (br. s., 1H), 8.20-8.50 (m, 1H), 8.50-8.83 (m, 1H), 12.18 (br. s., 1H). m/z (ESI) 412.3 (M+H)+.

Provenance & Evidence