2-Amino-5-bromopyridine → 2-Amino-5-methoxypyridine

Temperature

160 °C

Add 2-amino-5-bromopyridine (5.0 g, 29 mmol) to a freshly prepared solution of sodium methoxide (1.3 g, 58 mmol) in methanol (50 mL) and then add copper powder (1.8 g, 2.9 mmol). Heat and stir the mixture in a sealed tube at 160° C. for 3 days. Cool, filter through celite and concentrate under reduced pressure. Dissolve the residue in dichloromethane, then wash with water and saturated aqueous sodium chloride. Dry over magnesium sulfate, concentrate under reduced pressure, and subject the residue to silica gel chromatography, eluting with hexane/ethyl acetate; 3:1 to 0:1 to provide the title compound (1.5 g).

1. temperatureHeat
2. temperatureCool
3. filtrationfilter through celite
4. concentrationconcentrate under reduced pressure
5. dissolutionDissolve the residue in dichloromethane
6. washwash with water and saturated aqueous sodium chloride
7. dry with materialDry over magnesium sulfate
8. concentrationconcentrate under reduced pressure
9. washeluting with hexane/ethyl acetate

ORD record

ord-52bf1fc8c09b429cbe0fcb480d1d32fe

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022065B2