Benzenepropanoic acid, 3-bromo-3-oxo-, ethyl ester → 6-(3-Bromophenyl)-4-hydroxy-2-(4-phenoxyphenyl)nicotinonitrile

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Reaction Steps

A mixture of 3-amino-3-(4-phenoxyphenyl)acrylonitrile (0.553 g, 2342 mmol) and ethyl 3-(3-bromophenyl)-3-oxopropanoate (2.540 g, 9.37 mmol) was microwaved at 230° C. for 20 min. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate (100 mL). The ethyl acetate phase was washed with saturated ammonium chloride, brine, dried (MgSO4), and concentrated. Silica gel chromatography, eluting with 0-80% ethyl acetate in hexanes, gave 6-(3-bromophenyl)-4-oxo-2-(4-phenoxyphenyl)-1,4-dihydropyridine-3-carbonitrile as brown solid (0.909 g, 88% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.81 (1H, br. s), 7.70 (2H, δ, J=8.28 Hz), 7.62 (2H, δ, J=7.28 Hz), 7.35 (3H, t, J=7.40 Hz), 7.18 (1H, t, J=7.28 Hz), 7.03 (4H, dd, J=11.92, 8.66 Hz), 6.68 (1H, br. s); MS (ES+) m/z: 443,445 (M+H); LC retention time: 4.361 min (analytical HPLC Method A).

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