Phenethyl bromide → 3-Benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-phenethyl-1H-imidazol-2-yl)isophthalate

Participants

Reaction Steps

To a stirred solution of 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate (200 mg, 0.4 mmol) in dry DMF (5 mL) was added K2CO3 (168 mg, 1.22 mmol) and 2-phenethyl bromide (90 mg, 0.48 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred for 48 h. The reaction mixture was then cooled to 0° C., diluted with MTBE and quenched with water. The layers were separated and the aqueous layer was extracted with MTBE (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude oil. The crude material was purified by flash chromatography (gradient from 10% to 50% EtOAc/hexanes) to provide the title compound (175 mg, 72%). 1H NMR (CDCl3) 8.65 (d, J=2.0 Hz, 1H), 8.06 (dd, J=8.0, 2.0 Hz, 1H), 7.53 (s, 1H), 7.36-7.34 (m, 3H), 7.25-7.17 (m, 5H), 6.90 (d, J=8.0 Hz, 1H), 6.81-6.79 (m, 2H), 5.14 (s, 2H), 3.99 (s, 3H), 3.97-3.95 (m, 2H), 3.67 (t, J=7.2 Hz, 2H), 3.50 (br s, 2H), 2.76 (t, J=7.2 Hz, 2H), 1.70-1.60 (m, 4H), 1.40-1.20 (m, 4H), 0.98-0.84 (m, 6H); MS(ESI+) m/z 596.2 (M+H)+.

Provenance & Evidence