Methyl iodide → N-[2-(3-Cyano-5-fluorophenyl)-3-(4-methoxyphenyl)-1-methylpropyl]-2-(5-trifluoromethyl-2-pyridyloxy)-2-methylpropanamide

Participants

Reaction Steps

To a solution of N-[2-(3-cyano-5-fluorophenyl)-3-(4-hydroxyphenyl)-1-methylpropyl]-2-(5-trifluoromethyl-2-pyridyloxy)-2-methylpropanamide from Example 7, Step B (14 mg, 0.028 mmol) in 1.5 mL of dimethylformamide at 0° C. was added cesium carbonate (14 mg, 0.042 mmol) and methyl iodide (5 uL, 0.084 mmol), and the reaction was allowed to warm up to room temperature over 2 h. The resulting mixture was diluted with ether (20 mL), washed with water and brine and concentrated to dryness. The residue was purified by flash column chromatography eluting with 10 to 40% ethyl acetate in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ 8.27 (d, 1H), 7.96 (s, 1H), 7.94 (d, 1H), 7.93 (d, 1H), 7.29 (m, 1H), 7.18 (br s, 1H), 7.13 (m, 1H), 7.03 (d, 1H), 6.45 (ABq, 4H), 4.24 (m, 1H), 3.67 (s, 3H), 3.03 (dd, 1H), 2.88 (m, 1H), 2.57 (dd, 1H), 1.75 (s, 3H), 1.73 (s, 3H), 0.82 (d, 3H). LC-MS: m/e 530 (M+H)+ (3.9 min).

Provenance & Evidence