4-Fluorobenzyl bromide → N-Benzyl-5-(4-(4-fluorobenzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 9, making variations only as required to use 1-(bromomethyl)-4-fluorobenzene in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-benzyl-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide, the title compound was obtained as a pale yellow solid in 43% yield: mp 195-197° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.56 (t, J=6.0 Hz, 1H), 8.16 (d, J=8.0 Hz, 1H), 7.55-7.49 (m, 2H), 7.37-7.20 (m, 8H), 6.28 (dd, J=7.9, 2.7 Hz, 1H), 6.15 (d, J=2.7 Hz, 1H), 5.14 (s, 2H), 4.41 (d, J=6.0 Hz, 2H), 2.42 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.2, 162.4, 160.9, 139.6, 138.8, 137.2, 135.2, 135.1, 131.7 (d, JC-F=3.0 Hz), 130.4 (d, JC-F=8.4 Hz), 128.2, 127.3, 127.1, 126.6, 120.6, 115.3 (d, JC-F=21.5 Hz), 102.5, 97.3, 69.3, 42.5, 15.5; MS (ES+) m/z 449.3 (M+1).

Provenance & Evidence