4-Fluorobenzyl bromide → Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinate

Participants

Reaction Steps

Following the procedure as described in Preparation 17, making variations as required to replace 1-(bromomethyl)-4-fluorobenzene with (bromomethyl)cyclopropane to react with 2-(2-oxoimidazolidin-1-yl)isonicotinate, methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinate was obtained as a colorless solid in 69% yield: mp 75-77° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.69 (s, 1H), 8.42 (d, J=5.1 Hz, 1H), 7.35 (d, J=5.1 Hz, 1H), 3.94 (t, J=8.0 Hz, 2H), 3.85 (s, 3H), 3.54 (t, J=8.0 Hz, 2H), 3.06 (d, J=6.9 Hz, 2H), 0.97-0.87 (m, 1H), 0.49-0.43 (m, 2H), 0.22-0.15 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 165.8, 156.5, 153.8, 149.1, 138.4, 116.1, 111.4, 53.2, 48.2, 41.7, 41.5, 9.4, 3.6; MS (ES+) m/z 276.3 (M+1).

Provenance & Evidence