Acetic Acid → HCID 42630563, compound

Participants

Reaction Conditions

Reaction Steps

Benzofuran-5-carbaldehyde (330 mg, 2.19 mmol, 1.0 equiv.) and 4-aminopyridine (227 mg, 2.41 mmol, 1.1 equiv.) were combined in 1,2-dichloroethane (22 mL) and treated with acetic acid (138 μL, 2.41 mmol, 1.1 equiv.) and sodium triacetoxyborohydride (969 mg, 4.34 mmol, 1.98 equiv.). The mixture was stirred at 60° C. overnight, and then quenched by addition of saturated NaHCO3 solution. The two phases were separated and the water layer was extracted twice with ethyl acetate. The combined organic extract was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified with flash column chromatography on silica gel, eluting with ethyl acetate/dichloromethane/methanol to afford N-(benzofuran-5-ylmethyl)pyridin-4-amine as a white solid (62 mg, 13% yield). Mass: 225 (MH)+. Purity >99% (HPLC).

Provenance & Evidence