Bromine → 2-Bromo-6-methoxypyridin-3-amine

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Reaction Steps

Bromine (4.72 g, 29.5 mmol) is added to a mixture of 2-methoxy-5-aminopyridine (3.66 g, 29.5 mmol) and sodium acetate (4.84 g, 7.32 mmol) in acetic acid (50 mL) and stirred at rt for 20 minutes. Acetic acid is evaporated off in vacuo. The residue is dissolved in EtOAc (40 mL), and washed with water (40 mL), saturated sodium carbonate aqueous solution (20 mL), water (20 mL) and brine (20 mL). The organic layer is dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-40% EtOAc in heptane to afford 2-bromo-3-amino-6-methoxypyridine (4.35 g) as an oil. MS: 202 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.89 (s, 3H), 6.60(d, H), 7.07(d, H).

Provenance & Evidence