Dimethylformamide → Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-oxoimidazolidin-1-yl)isonicotinate (10.00 g, 45.20 mmol) in N,N-dimethylformamide (300 mL) was added sodium hydride (60% dispersion in mineral oil, 1.90 g, 45.20 mmol) at 0° C. The resulting solution was stirred for 30 minutes at 0° C., followed by the addition of 1-(bromomethyl)-4-fluorobenzene (8.54 g, 45.20 mmol). The reaction mixture was warmed to ambient temperature, stirred for 17 hours and concentrated in vacuo to dryness. The residue was purified by column chromatography eluted with dichloromethane and ethyl acetate to give methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate as a colorless solid (10.03 g, 67%): mp 119-121° C.; 1H NMR (300 MHz, CDCl3) δ 8.87 (d, J=0.6 Hz, 1H), 8.35 (d, J=5.4 Hz, 1H), 7.45-7.43 (m, 1H), 7.29-7.25 (m, 2H), 7.04-6.98 (m, 2H), 4.44 (s, 2H), 4.20 (t, J=7.8 Hz, 2H), 3.91 (s, 3H), 3.35 (t, J=7.8 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.9, 164.0, 160.7, 156.8, 153.4, 148.0, 138.7, 132.3, 130.0, 116.7, 115.8, 115.5, 112.5, 52.6, 47.8, 41.3, 41.0; MS (ES+) m/z 330.2 (M+1).

Provenance & Evidence