4-Fluorobenzyl bromide → Methyl 2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-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 4-(bromomethyl)pyridine hydrobromide to react with 2-(2-oxoimidazolidin-1-yl)isonicotinate, methyl 2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl)isonicotinate was obtained as a colorless solid in 43% yield: mp 111-113° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.73 (s, 1H), 8.51 (d, J=5.7 Hz, 2H), 8.45-8.44 (m, 1H), 7.40-7.38 (m, 1H), 7.30 (d, J=6.0 Hz, 2H), 4.44 (s, 2H), 3.99 (t, J=7.9 Hz, 2H), 3.86 (s, 3H), 3.42 (t, J=7.9 Hz, 2H); 13C NMR (75 MHz, DMSO-d6) δ 165.7, 156.9, 153.7, 150.3, 149.1, 146.6, 138.5, 123.0, 116.4, 111.5, 53.2, 46.4, 41.7, 39.1; MS (ES+) m/z 312.9 (M+1).

Provenance & Evidence