Benzoyl chloride → N-(4-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-yl)phenyl)benzamide

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Reaction Steps

Benzoyl chloride (10 μL, 0.086 mmol was added to a mixture of 6-(4-aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile (13 mg, 0.033 mmol, from Step 3 of Example 199) and Hunig's base (30 μL, 0.172 mmol) in dichloromethane (0.6 mL). After 16 h at room temperature, the reaction was complete as judged by LCMS analysis. Silica gel chromatography, eluting with 0-50% ethyl acetate in hexanes, gave N-(4-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-yl)phenyl)benzamide as yellow solid (17.6 mg, 100% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.18 (2H, δ, J=8.53 Hz), 8.02-8.06 (2H, m), 7.97 (1H, s), 7.91 (2H, δ, J=7.28 Hz), 7.80-7.87 (3H, m), 7.57-7.63 (1H, m), 7.53 (2H, t, J=7.40 Hz), 7.38-7.44 (2H, m), 7.19 (1H, t, J=7.40 Hz), 7.09-7.17 (4H, m); MS (ES+) m/z: 502 (M+H); LC retention time: 4.923 min (analytical HPLC Method A).

Provenance & Evidence