Phosphorus oxychloride → 4-Chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile

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A mixture of 6-(4-nitrophenyl)-4-oxo-2-(4-phenoxyphenyl)-1,4-dihydropyridine-3-carbonitrile (211 mg, 0.515 mmol) and phosphoryl trichloride (1 mL, 10.92 mmol) was heated to 95° C. for 30 min, then concentrated. The residue was dissolved in dichloromethane (2 mL) and washed with saturated sodium bicarbonate. Silica gel chromatography, eluting with 0-100% ethyl acetate in hexanes, gave 4-chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile as white solid (136.3 mg, 62% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.35-8.41 (2H, m), 8.27-8.33 (2H, m), 8.00-8.06 (2H, m), 7.91 (1H, s), 7.38-7.46 (2H, m), 7.21 (1H, t, J=7.40 Hz), 7.10-7.18 (4H, m); MS (ES+) m/z: 428 (M+14); LC retention time: 4.141 min (analytical HPLC Method A).

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