Sodium hydride → HCID 24986110, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylate (1.00 g, 3.56 mmol) in N,N-dimethylformamide (10 mL) at 0° C. was added sodium hydride (0.14 g, 5.70 mmol). The reaction mixture was stirred at 0° C. for 30 minutes, then (bromomethyl)cyclopropane (0.58 g, 4.28 mmol) was added. The reaction mixture was stirred at ambient temperature for 16 hours. The solvent was removed at high vacuum and the residue was diluted with dichloromethane (30 mL), washed with brine (25 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography eluting with ethyl acetate/hexane (1/1) to afford the title compound as a colorless solid (1.15 g, 97%): mp 180-183° C. (hexane/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.68-8.65 (m, 1H), 6.19-6.16 (m, 1H), 5.93 (d, J=2.6 Hz, 1H), 4.31 (q, J=7.1 Hz, 2H), 3.81 (d, J=7.1 Hz, 2H), 2.68 (s, 3H), 1.35 (t, J=7.1 Hz, 3H), 1.31-1.19 (m, 1H), 0.70-0.64 (m, 2H), 0.38-0.33 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 167.6, 162.9, 162.2, 156.6, 155.6, 131.3, 119.6, 104.5, 96.7, 60.9, 17.3, 14.3, 9.8, 9.5, 3.3; MS (ES+) m/z 335.1 (M+1).

Provenance & Evidence