Sodium Iodide → HCID 69068939, compound

Participants

Reaction Conditions

Reaction Steps

A 0.2M DMF solution of methyl 1-(4-hydroxyphenyl)-1H-benzimidazole-5-carboxylate (3.0 g, 9.8 mmol) with KOtBu (2.2 g, 19.6 mmol) was stirred at rt for 20 min. prior to treatment with NaI (9.8 mmol, 1.47 g) and p-(trifluoromethoxy) benzylbromide (1.88 mL, 11.2 mmol). The mixture was heated at 60° C. for 24 h. after which the mixture was concentrated in vacuo, and the residue purified by chromatography over silica gel eluting with 1:1 EtOAc:Hexane to afford methyl 1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxylate. 1H NMR (DMSO-d6, 400 MHz) δ 3.89 (s, 3H), 5.26 (s, 2H), 7.26-7.29 (m, 2H), 7.43 (d, 2H, J=7.6 Hz), 7.61-7.65 (m, 5H), 7.86 (dd, 1H, J=8.8 Hz, 1.6 Hz), 8.35 (d, 1H, J=1.2 Hz), 8.65 (s, 1H); MS (ES+): m/z 443 (MH+).

Provenance & Evidence