4-(Difluoromethoxy)benzyl Bromide → 2-(4-(4-(Difluoromethoxy)benzyloxy)-2-oxopyridin-1(2H)-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 9, making variation only as required to use 4-(difluoromethoxy)benzyl bromide in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-(4-fluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 25% yield: mp 242-244° C. (dichloromethane/methanol); 1H NMR (300 MHz, DMSO-d6) δ 8.78 (t, J=5.8 Hz, 1H), 8.60 (dd, J=8.1, 3.0 Hz, 1H), 7.56-7.47 (m, 2H), 7.34-7.08 (m, 7H), 6.43-6.32 (m, 1H), 6.22 (s, 1H), 5.15 (s, 2H), 4.34 (d, J=5.8 Hz, 2H), 2.52 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.4, 163.2, 161.9, 160.0, 151.4, 150.4, 136.1, 133.7, 132.7, 130.5, 129.8, 123.6, 120.1, 119.2, 116.7, 115.6, 113.3, 104.3, 97.5, 70.1, 44.6, 17.5; MS (ES+) m/z 516.4 (M+1).

Provenance & Evidence