Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1) → HCID 10192781, compound

Temperature

-78 °C

3-(1H-1,2,3-Triazol-4-yl)benzonitrile (1.82 g, 10.69 mmol) was suspended in anhydrous MeOH (25 mL) under argon at ambient temperature. To this was added NaOMe (21.4 mL of 0.5 M solution in MeOH, 10.69 mmol), and the resulting reaction mixture was cooled to −78° C. A solution of N-fluoropyridinium triflate (2.95 g, 8.91 mmol) in anhydrous MeOH (5 mL) was then added dropwise via syringe. The reaction mixture was stirred at −78° C. for 30 min, then warmed to ambient temperature and stirred for an additional 18 h. The reaction mixture was partitioned between EtOAc (300 mL) and 1N aqueous NaOH (100 mL). The EtOAc layer was washed with additional 1N aqueous NaOH (6×50 mL). The EtOAc layer was dried (MgSO4), filtered and concentrated in vacuo. The resulting crude material was then chromatographed on silica gel eluting with hexanes:EtOAc (2:1) to afford EXAMPLE 5 3-(2-pyridin-2-yl-2H-1,2,3-triazol-4-yl)benzonitrile as a tan solid.

1. customthe resulting reaction mixture
2. temperaturewarmed to ambient temperature
3. stirringstirred for an additional 18 h
4. customThe reaction mixture was partitioned between EtOAc (300 mL) and 1N aqueous NaOH (100 mL)
5. washThe EtOAc layer was washed with additional 1N aqueous NaOH (6×50 mL)
6. dry with materialThe EtOAc layer was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting crude material was then chromatographed on silica gel eluting with hexanes:EtOAc (2:1)

ORD record

ord-b86fc58180334b4188d2208f8e58f913

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105548B2