1-(Bromomethyl)-4-(trifluoromethyl)benzene → HCID 24801326, compound

Participants

Reaction Steps

Following the procedure as described in Example 2, making variation as required to use N-(3-fluorobenzyl)-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide in place of N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide to react with 1-(bromomethyl)-4-(trifluoromethyl)benzene, the title compound was obtained as a white solid in 41% yield: mp 177-178° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.52 (d, J=8.1 Hz, 2H), 7.30-7.27 (m, 3H), 7.10-6.92 (m, 3H), 6.11 (t, J=5.6 Hz, 1H), 4.56 (d, J=5.6 Hz, 2H), 4.33-4.21 (m, 1H), 4.00-3.88 (m, 1H), 3.53-3.56 (m, 1H), 2.94-2.73 (m, 2H), 2.62 (s, 3H), 2.11-1.95 (m, 1H), 1.94-1.75 (m, 2H), 1.62-1.43 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 171.7, 162.9, 162.7, 156.9, 152.4, 143.2, 140.6, 130.3, 129.6, 128.9, 125.9, 125.5, 125.4, 123.3, 122.4, 119.3, 114.7, 114.5, 48.0, 43.9, 43.3, 37.3, 24.9, 21.3, 17.4; MS (ES+) m/z 506.3 (M+1).

Provenance & Evidence