1-(Bromomethyl)-4-(trifluoromethyl)benzene → N-Benzyl-4-methyl-2-(2-oxo-4-(4-(trifluoromethyl)benzyloxy)pyridin-1(2H)-yl)thiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 9, making variations only as required to use 4-trifluoromethylbenzyl bromide in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 21% yield: mp 278-280° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.78 (br s, 1H), 8.65-8.62 (m, 1H), 7.78-7.64 (m, 4H), 7.30-7.29 (m, 5H), 6.44-6.41 (m, 1H), 6.23 (d, J=2.7 Hz, 1H), 5.30 (s, 2H), 4.38 (d, J=6.0 Hz, 2H), 2.54 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.3, 161.9, 161.6, 153.9, 150.4, 140.7, 139.9, 132.3, 128.8, 128.7, 127.7, 127.2, 126.4, 126.0, 125.9, 123.8, 104.3, 97.7, 69.8, 43.1, 17.5; MS (ES+) m/z 500.3 (M+1).

Provenance & Evidence