Methanol → 1-(4-bromo-2-fluorophenyl)-3-methyl-1H-1,2,4-triazole

To a mixture of (4-bromo-2-fluorophenyl)hydrazine (3.4 g) in methanol (25 mL) was added methyl ethanimidothioate hydroiodide (3.6 g), and the mixture was stirred at room temperature for 40 min. The solvent was evaporated under reduced pressure. To a mixture of the obtained residue in toluene (20 mL) were added methyl orthoformate (15 mL) and pyridine (15 mL), and the mixture was stirred at 100° C. for 9 hr. The reaction mixture was allowed to cool to room temperature, and diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, the organic layer 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 (3.7 g).

1. customThe solvent was evaporated under reduced pressure
2. additionTo a mixture of the obtained residue in toluene (20 mL)
3. additionwere added methyl orthoformate (15 mL) and pyridine (15 mL)
4. stirringthe mixture was stirred at 100° C. for 9 hr
5. temperatureto cool to room temperature
6. additiondiluted with saturated aqueous sodium hydrogen carbonate solution
7. extractionthe mixture was extracted with ethyl acetate
8. washThe extract was washed with saturated brine
9. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
10. customthe solvent was evaporated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-9dec70ab15444c42849a5ed0a6bae456

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822699B2