4-Fluorobenzyl bromide → Methyl 2-(2-oxo-3-(pyridin-3-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 3-(bromomethyl)pyridine hydrobromide to react with 2-(2-oxoimidazolidin-1-yl)isonicotinate, methyl 2-(2-oxo-3-(pyridin-3-ylmethyl)imidazolidin-1-yl)isonicotinate was obtained as a colorless solid in 47% yield: mp 165-167° C.; 1H NMR (300 MHz, CDCl3) δ 8.86 (s, 1H), 8.56-8.54 (m, 2H), 8.36 (d, J=5.1 Hz, 1H), 7.69-7.66 (m, 1H), 7.46 (dd, J=5.4 Hz, 1.5 Hz, 1H), 7.30-7.26 (m, 1H), 4.50 (s, 2H), 4.05 (t, J=8.1 Hz, 2H), 3.92 (s, 3H), 3.39 (t, J=8.1 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.8, 156.9, 153.2, 149.6, 149.4, 148.0, 138.8, 136.0, 132.1, 123.8, 116.9, 112.5, 52.6, 45.5, 41.3, 41.2; MS (ES+) m/z 312.9 (M+1).

Provenance & Evidence