Ethyl Acetate → N-(5-bromo-2-methoxypyridin-3-yl)acetamide

Participants

Reaction Steps

A suspension of 5-bromo-2-methoxy-3-nitro-pyridine (Stage 63.1.4, 450 mg, 1.93 mmol) and tin dichloride (1.465 mg, 7.72 mmol) in EtOAc (30 ml) was refluxed for 3 h. The reaction mixture was evaporated to dryness and then quenched with cold 3 M aqueous NaOH (50 ml) and CH2Cl2 (50 ml) and stirred for 3 h at rt. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with 30 ml sat. aqueous NaHCO3, dried over Na2SO4, filtered and evaporated. The crude product was dry loaded on silica gel and purified by MPLC (CH2Cl2/MeOH 0% to 4%) to give after evaporation the title compound as an off-white solid (HPLC: tR 2.72 min (Method A); M+H=245, 247 MS-ES).

Provenance & Evidence