Potassium Carbonate → 4-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-[(5-methyl-2-oxo-3-{5-[2-(trifluoro-methoxy)phenyl]pyridin-2-yl}-1,3-oxazolidin-5-yl)methyl]benzamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-{[3-(5-chloropyridin-2-yl)-5-methyl-2-oxo-1,3-oxazolidin-5-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide (26 mg, EXAMPLE 50) and potassium carbonate (35 mg) in 0.5 ml of tetrahydrofuran and 0.5 ml of water was added 2-trifluoromethoxyphenylboronic acid (10 mg) and palladium di-tert-butylphosphinoferrocene (7 mg). The mixture was heated via microwave for 10 min at 100° C. The sample was cooled to room temperature, and was purified via column chromatography on a Biotage Horizon 40M column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 100% ethyl acetate in hexanes (over 10 column volumes), and held at 100% ethyl acetate for 4 column volumes to provide the title compound as an off-white solid (8 mg, 24%). Mass spectrum (ESI) 656.4 (M+1). 1H NMR (500 MHz, CDCl3):): δ 8.40 (d, J=2.0 Hz, 1H), 8.31 (d, J=8.3 Hz, 2H), 8.25 (d, J=8.7 Hz, 1H), 7.95 (d, J=8.5 Hz, 2H), 7.92 (s, 1H), 7.82 (dd, J=8.7, 2.3 Hz, 1H), 7.51 (s, 1H), 7.40 (m, 4H), 6.82 (t, J=6.3 Hz, 1H), 4.30 (d, J=10.7 Hz, 1H), 4.13 (d, J=10.8 Hz, 1H), 3.94 (dd, J=14.5, 6.3 Hz, 1H), 3.86 (dd, J=14.5, 6.5 Hz, 1H), 3.47 (sept, J=6.9 Hz, 1H), 1.65 (s, 3H), 1.45 (d, J=6.9 Hz, 6H).

Provenance & Evidence