Sodium Carbonate → HCID 89813741, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with (S)-3-(4-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.074 g, 0.152 mmol), 2-chloropyrimidine-4-carbonitrile (commercially available from Synthonix, Wake Forest, N.C.)(0.023 g, 0.167 mmol), sodium carbonate (0.048 g, 0.455 mmol), dioxane (2.0 mL), and water (0.400 mL). Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) DCM adduct (0.012 g, 0.015 mmol) was added, the system was purged with argon, and the tube was sealed. The mixture was then stirred at 100° C. in a microwave for 1 hour. The resulting reaction mixture was filtered through Celite® brand filter aid and the filtrate was concentrated to afford a brown solid. The resulting solid was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% EtOAc-hexane) to afford (S)-2-(5-(4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)phenyl)-6-fluoropyridin-3-yl)pyrimidine-4-carbonitrile (0.051 g, 0.110 mmol, 72.3% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 3H), 1.66 (s, 3H), 5.53 (s, 1H), 7.14-7.50 (m, 5H), 7.59-7.78 (m, 4H), 8.17 (d, J=4.99 Hz, 1H), 8.78 (dd, J=9.68, 2.35 Hz, 1H), 9.09 (dd, J=2.30, 0.93 Hz, 1H), 9.29 (d, J=4.89 Hz, 1H). m/z (ESI) 466 (M+H)+.

Provenance & Evidence