Hydrochloric Acid → HCID 86731314, compound

Temperature

70 °C

To a solution of methyl 4-fluoro-5-(methoxymethoxy)pyridine-2-carboxylate (1.80 g) in THF (20 mL) was added 6 N hydrochloric acid (5 mL), and the mixture was stirred at 70° C. for 20 min. To the reaction mixture was added saturated brine, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in DMF (20 mL), potassium carbonate (2.31 g) and (bromomethyl)cyclopropane (1.22 mL) were added thereto, and the mixture was stirred with heating at 70° C. for 1 hr. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.07 g).

1. extractionthe mixture was extracted with ethyl acetate
2. dry with materialThe extract was dried over anhydrous magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in DMF (20 mL)
5. additionpotassium carbonate (2.31 g) and (bromomethyl)cyclopropane (1.22 mL) were added
6. stirringthe mixture was stirred
7. temperaturewith heating at 70° C. for 1 hr
8. temperatureto cool to room temperature
9. additiondiluted with ethyl acetate
10. washwashed with saturated brine
11. dry with materialdried over anhydrous magnesium sulfate
12. customthe solvent was evaporated under reduced pressure
13. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-88901cad6abd4afeaa456df2b9f26083

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133129B2