Reaction Steps
Yield 40%. α-[[(4-Chlorophenyl)amino]methylene]-N-(4-fluorophenyl)-3-methyl-5-isoxazoleacetamide: Yield 44%, 1H NMR (400 MHz, CDCl3) δ 11.50 (d, 1H), 8.28 (s, 1H), 7.70 (d, 1H), 7.50 (d, 2H), 7.30 (d, 4H), 7.00 (d, 2H), 6.01, 6.20 (s, 1H), 2.30, 2.35 (s, 3H); TOF MS ES+ m/z 372, 374 (MH+); 394, 396 (M+Na+); α-[[(4-Ethoxyphenyl)amino]methylene]-N-(4-fluorophenyl)-3-methyl-5-isoxazoleacetamide: Yield 47%; 1H NMR (400 MHz, CDCl3) δ 11.40 (d, 1H, J=12.3 Hz), 8.26 (br s, 1H), 7.67 (d, 1H, J=12.9 Hz), 7.48 (d, 2H, J=9.1 Hz), 7.04 (d, 2H, J=8.9 Hz), 7.01 (d, 2H, J=8.9 Hz), 6.98 (d, 2H, J=8.9 Hz), 5.95 (s, 1H), 4.00 (q, 2H, J=6.9 Hz), 2.31 (s, 3H), 1.40 (t, 2H, J=6.9 Hz); N-(4-Chlorophenyl)-α-[(3-fluorophenylamino)methylene]-3-methyl-5-isoxazole-acetamide; Isolated in 44% yield. 1H NMR (400 MHz, CDCl3) δ 11.50 (d, 1H), 8.30, 8.15 (d, 1H), 7.70 (d, 1H), 7.50 (d, 2H), 7.30 (dd, 3H), 6.80 (m, 3H), 6.22, 6.02 (s, 1H), 2.35, 2.30 (s, 3H). TOF MS ES+ m/z 372, 374 (M+H+) 394, 396 (M+Na+).
