Phosphorus oxychloride → Methyl 4-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-yl)benzoate

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Reaction Conditions

Reaction Steps

A mixture of methyl 4-(5-cyano-4-oxo-6-(4-phenoxyphenyl)-1,4-dihydropyridin-2-yl)benzoate (598.2 mg, 1.416 mmol) and phosphoryl trichloride (12 mL) was heated to 90° C. for 1 h then concentrated. The residue was dissolved in dichloromethane, washed with water and concentrated. Silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes, gave methyl 4-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-yl)benzoate as white solid (0.5582 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.19 (4H, s), 8.01-8.06 (2H, m), 7.89 (1H, s), 7.38-7.44 (2H, m), 7.20 (1H, t, J=7.40 Hz), 7.10-7.17 (4H, m), 3.97 (3H, s), MS (ES+) m/z: 441 (M+H); LC retention time: 4.333 min (analytical HPLC Method A).

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