Vinyl Acetate → 2-fluoro-5-(1H-1,2,3-triazol-1-yl)pyridine

HRID 1798819Notes

Reaction equation

HRID 1798819 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([F:10])=[N:8][CH:9]=1)=[N+:2]=[N-:3].[C:11](OC=C)(=O)[CH3:12]>>[N:1]1([C:4]2[CH:5]=[CH:6][C:7]([F:10])=[N:8][CH:9]=2)[CH:12]=[CH:11][N:3]=[N:2]1

Participants

3

Reactant 2

HCID 7904Vinyl AcetateHCID 581285335-Azido-2-fluoropyridine

Product 1

HCID 581285562-fluoro-5-(1H-1,2,3-triazol-1-yl)pyridine

Conditions

Temperature
100 °C

Procedure

5-Azido-2-fluoropyridine (262 mg, 1.9 mmol) and vinyl acetate (4.0 mL, 43 mmol) were mixed in a flame dried high pressure sealable vessel. The reaction vessel was evacuated and charged with nitrogen, sealed, and heated to 100° C. for 15 hours. The reaction was cooled to room temperature and TLC indicated that the reaction was complete. Minimal dichloromethane was added to the reaction (just enough to dissolve solids that formed upon cooling) and the solution directly chromatographed on silica gel (Biotage size 40S column), eluting with 20-50% ethyl acetate/heptane to give the title compound as a white solid.

Workup

  1. customdried high pressure sealable vessel
  2. customThe reaction vessel was evacuated
  3. additioncharged with nitrogen
  4. customsealed
  5. temperatureThe reaction was cooled to room temperature
  6. additionMinimal dichloromethane was added to the reaction (just enough
  7. dissolutionto dissolve solids that
  8. customformed
  9. temperatureupon cooling) and the solution
  10. customdirectly chromatographed on silica gel (Biotage size 40S column)
  11. washeluting with 20-50% ethyl acetate/heptane

Sources & evidence

ORD record
ord-e1d406e454874585a0a0cdc43f1834c4
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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