Stannous Chloride → 5-Bromo-2-ethoxypyridin-3-amine

Participants

Reaction Steps

A solution of 5-bromo-2-(ethyloxy)-3-nitropyridine (15.5 g) in EtOAc (300 ml) was treated with tin(II) chloride anhydrate (56.6 g) then heated at reflux for 2.5 hr. The reaction was cooled to RT then evaporated to dryness. The residue was treated with 2M NaOH (aq) (500 ml) that was treated with anhydrous magnesium sulfate (˜50 g) then slurried to give a filterable sludge. The filtrate was separated and the organic phase was washed with brine, dried over magnesium sulfate then evaporated to dryness. The residue was purified by column chromatography on silica, eluting with DCM, to give the title compound.

Provenance & Evidence