Sodium Carbonate → (S)-3-(4-(6-fluoro-[3,3'-bipyridin]-5-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with (S)-3-(4-(5-bromo-2-fluoropyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (Example 3)(0.040 g, 0.091 mmol), 3-pyridylboronic acid (commercially available from Sigma-Aldrich, Milwaukee, Wis., 0.022 g, 0.181 mmol), sodium carbonate (0.029 g, 0.272 mmol), dioxane (2.0 mL), and water (0.40 mL). Tetrakis(triphenylphosphine)-palladium(0) (10.47 mg, 9.06 mol) 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. The reaction mixture was next filtered through Celite® brand filter aid and the filtrate was concentrated to afford a yellow oil. The oil thus obtained was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 50-100% EtOAc-hexane) to afford (S)-3-(4-(6-fluoro-[3,3′-bipyridin]-5-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.033 g, 0.075 mmol, 83% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 3H), 1.65 (s, 3H), 5.53 (s, 1H), 7.24-7.45 (m, 5H), 7.51 (ddd, J=8.00, 4.82, 0.88 Hz, 1H), 7.60-7.75 (m, 4H), 8.23 (ddd, J=8.00, 2.42, 1.61 Hz, 1H), 8.41 (dd, J=9.63, 2.49 Hz, 1H), 8.56 (dd, J=2.40, 1.32 Hz, 1H), 8.62 (dd, J=4.74, 1.61 Hz, 1H), 9.02 (dd, J=2.45, 0.78 Hz, 1H). m/z (ESI) 440 (M+H)+.

Provenance & Evidence