Acetyl chloride → HCID 66926924, compound

Participants

Reaction Steps

Acetyl chloride (0.013 mL, 0.181 mmol) was added to a suspension of 6-(4-aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile (48 mg, 0.121 mmol, from Step 3 of Example 199) and Hunig's base (0.084 mL, 0.483 mmol) in dichloromethane (1 mL) at room temperature. After 90 min at room temperature, additional acetyl chloride (0.05 mL) was added. After additional 23 h, the reaction was stopped and the mixture purified by silica gel chromatography, eluting with 0-60% ethyl acetate in hexanes, to give N-(4-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-yl)phenyl)acetamide as yellow solid (24.9 mg, 47% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (2H, δ, J=8.78 Hz), 8.00-8.03 (2H, m), 7.79 (1H, s), 7.68 (2H, δ, J=8.53 Hz), 7.35-7.44 (3H, m), 7.19 (1H, t, J=7.40 Hz), 7.08-7.15 (4H, m), 2.23 (3H, s); MS (ES+) m/z: 440 (M+H); LC retention time: 4.668 min (analytical HPLC Method A). Unreacted starting material was also recovered (13.7 mg).

Provenance & Evidence