Potassium Carbonate → HCID 11578015, compound

Participants

Reaction Steps

A mixture of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-(2-bromo-5-chlorobenzyl)-4-methyl-1,3-oxazolidin-2-one (44 mg, 0.085 mmol), (4-fluoro-5-isopropyl-2-methoxyphenyl)boronic acid (Example 78, 23 mg, 0.11 mmol), potassium carbonate (25 mg, 0.18 mmol) and catalytic amount of PdOAc in a 4:1 mixture of acetone/water was heated to reflux for 1 h. Acetone was removed and water was added. The organic was extracted with methylene chloride (3×15 ml). The combined methylene chloride layers were washed with brine and dried over sodium sulfate. The title compound was obtained as a solid after preparative reverse phase HPLC. 1H NMR (CDCl3, 500 MHz) δ 1:1 mixture of rotamer δ 7.90 (s, 1H), 7.73 (s, 2H), 7.49 (m, 1H), 7.40 (m, 1H), 7.20 (m, 1H), 7.00 (m, 1H), 6.68 (dd, J=12.0, 3.0 Hz, 1H), 5.63 (d, J=8.0 Hz, ½ H), 5.44 (d, J=8.0 Hz, ½ H), 4.85 (d, J=10.0 Hz, ½ H), 4.82 (d, J=10.0 Hz, ½ H), 4.03 (d, J=16.0 Hz, ½ H), 3.84 (m, 1½ H), 3.80 (s, 3H), 3.20 (m, 1H), 1.20 (m, 6H), 0.56 (d, J=6.5 Hz, 3/2 H), 0.38 (d, J=6.5H, 3/2 H). LC-MS (M+1): 604.3, 4.61 min.

Provenance & Evidence