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

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).

1. customAcetic acid is evaporated off in vacuo
2. dissolutionThe residue is dissolved in EtOAc (40 mL)
3. washwashed with water (40 mL), saturated sodium carbonate aqueous solution (20 mL), water (20 mL) and brine (20 mL)
4. dry with materialThe organic layer is dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue is purified by silica gel chromatography
8. washeluting with 0-40% EtOAc in heptane

ORD record

ord-3c4086a7c7024e90b5381e9513b6b774

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258130B2