Nitrogen → HCID 58278823, compound

Participants

Reaction Steps

A mixture containing 2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-amine (13; 120 mg, 0.43 mmol), nicotinaldehyde (16; 51 mg, 0.47 mmol) and NaBH(OAc)3 (143 mg, 0.67 mmol) in 1,2-dichloroethane (10 mL) was stirred at room temperature for 12 h under an inert atmosphere of N2. Saturated aqueous NaHCO3 (10 mL) was added and the mixture was extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (gradient elution, petroleum ether:ethyl acetate=1:1 to 1:3) to afford N-(pyridin-3-ylmethyl)-2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-amine (Compound) (70 mg, 0.198 mmol, 46%) as a pale yellow solid. MS (ESI) calcd for C20H15F3N4: 368.12; found: 369 [M+H].

Provenance & Evidence