Sodium hydride → N-Benzyl-4-methyl-2-(2-oxo-4-(pyridin-3-ylmethoxy)pyridin-1(2H)-yl)thiazole-5-carboxamide

Participants

Reaction Steps

To a solution of N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide (0.10 g, 0.29 mmol) in N,N-dimethylformamide (4 mL) was added sodium hydride (60% dispersion in mineral oil, 0.028 g, 0.70 mmol) slowly at 0° C. The reaction mixture was stirred for 5 minutes and then 3-(bromomethyl)pyridine hydrobromide (0.096 g, 0.38 mmol) and tetra-n-butylammonium iodide (0.005 g, 0.014 mmol) were added at 0° C. After stirred at ambient temperature for 16 hours, the reaction mixture was concentrated in vacuo to yield a solid residue. The crude product was purified by column chromatography eluted with ethyl acetate/hexanes (50/50 to 100/0) to afford the title compound as a white solid (0.018 g, 14% yield): mp 214-216° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.81-8.61 (m, 4H), 7.98 (d, J=7.8 Hz, 1H), 7.55-7.51 (m, 1H), 7.33-7.19 (m, 5H), 6.42-6.39 (m, 1H), 6.28 (d, J=2.7 Hz, 1H), 5.25 (s, 2H), 5.39 (d, J=5.7 Hz, 2H), 2.55 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.3, 161.9, 161.6, 153.9, 150.3, 149.1, 148.7, 139.9, 137.8, 132.3, 128.8, 127.7, 127.2, 124.7, 123.8, 104.3, 97.7, 68.3, 17.5; MS (ES+) m/z 433.2 (M+1).

Provenance & Evidence