Acetic Acid → (S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-((4-(hydroxymethyl)benzoyl)oxy)ethyl)pyridine 1-oxide

Participants

Reaction Steps

To a stirred solution of (S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-((4-formylbenzoyl)oxy)ethyl)pyridine 1-oxide (412 mg, 0.87 mmol) in DCM (10 mL) was added 3-aminopyridazine (165 mg, 1.73 mmol) followed by glacial acetic acid (150 μL, 2.61 mmol). The reaction was stirred at room temperature for 30 minutes then NaB(OAc)3H (551 mg, 2.61 mmol) was added. The reaction mixture was stirred at room temperature for 18 hours. The reaction was diluted with DCM (10 mL) and quenched with water. The organic phase was washed with saturated aqueous NaHCO3 solution, filtered through hydrophobic fit and evaporated to dryness. The residue was triturated with DCM (2 mL) and CH3CN (5 mL). The solid was collected by filtration, washed with DCM and dried to provide the title compound (300 mg, 72%) as white solid.

Provenance & Evidence