Sodium borohydride → N-[(2-chloro-5-thiazolyl)methyl]-3-phenyl-2-pyridinamine

Participants

Reaction Steps

N-[(2-chloro-5-thiazolyl)methylene]-3-phenyl-2-pyridinamine (i.e. the product of Step B) was added portionwise to a stiffed excess of sodium borohydride (0.379 g, 100 mmol) in methanol (8 mL). After addition was complete, the reaction mixture was allowed to stir for 5 min at ambient temperature. The excess reducing agent was quenched by adding glacial acetic acid until gas evolution ceased. Water (20 mL) was added, and the reaction mixture was concentrated to remove methanol. The resulting aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried (MgSO4) and concentrated to give the title compound as a yellow solid (0.659 g).

Provenance & Evidence