Potassium Iodide → 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

To a mixture of N-(6-bromo-2-methoxypyridin-3-yl)formamide (8.0 g), cesium carbonate (20.1 g) and potassium iodide (580 mg) in DMF (40 mL) was added 1-chloropropan-2-one (4.13 mL), and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Acetic acid (50 mL) and ammonium acetate (26.7 g) were added to the residue, and the mixture was stirred at 130° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. Water was added, and the mixture was neutralized with aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.72 g).

1. customThe solvent was evaporated under reduced pressure, water
2. additionwas added
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. additionAcetic acid (50 mL) and ammonium acetate (26.7 g) were added to the residue
8. stirringthe mixture was stirred at 130° C. for 3 hr
9. temperatureto cool to room temperature
10. customthe solvent was evaporated under reduced pressure
11. additionWater was added
12. extractionextracted with ethyl acetate
13. dry with materialThe extract was dried over anhydrous magnesium sulfate
14. customthe solvent was evaporated under reduced pressure
15. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-c199a4d668fb4c39a80174b93f5a2aff

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822699B2