Water → HCID 86672713, compound

Participants

Reaction Steps

The solution of methyl 1-(2,2-dimethoxyethyl)-2-(4-fluorophenyl)-1H-benzo[d]imidazole-7-carboxylate (1.1 g, 3.1 mmol) from Step A above in 1,2-dichloroethane (5 mL) with water (3 mL) and trifluoroacetic acid (3 mL) was stirred at reflux for 2.5 h. The reaction mixture was concentrated under reduced pressure, the residue was diluted with methylene chloride, neutralized with saturated aqueous sodium bicarbonate, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford methyl 2-(4-fluorophenyl)-1-(2-oxoethyl)-1H-benzo[d]imidazole-7-carboxylate (820 mg, 84%) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 9.80 (s, 1H), 8.05 (d, J=8.0, Hz, 1H), 7.98 (d, J=7.5, Hz, 1H), 7.62 (dd, J=7.5, 5.0 Hz, 2H), 7.36 (t, J=8.0 Hz, 1H), 7.21 (t, J=7.5 Hz, 2H), 5.25 (s, 2H), 3.92 (s, 3H); MS (ESI+) m/z 313 (M+H).

Provenance & Evidence