1H-Imidazole-4-carbaldehyde → (3-Benzyloxy-phenyl)-(6-bromo-pyridin-2-ylmethyl)-(3H-imidazol-4-ylmethyl)-amine

Participants

Reaction Conditions

Reaction Steps

(3-Benzyloxy-phenyl)-(6-bromo-pyridin-2-ylmethyl)-amine (0.10 g, 0.27 mmol) was dissolved in methanol (2 ml). Then 4-formylimidazole (0.13 g, 1.35 mmol), zinc chloride (0.15 g, 1.08 mmol) and sodium cyanoborohydride (0.05 g, 0.81 mmol) were added and the reaction mixture was allowed to stir at 40° C. overnight. After cooling, the reaction mixture was poured onto ammoniumchloride/ice and extracted with ethyl acetate (2 times 50 ml). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (SiO2; eluent: methanol/dichloromethane=1:9) to yield an off-white gum (0.11 g, 94%); MS (ISP): 451.1 ([81Br M+H]+), 449.1 ([79Br M+H]+).

Provenance & Evidence