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

HRID 1039058Notes

Reaction equation

HRID 1039058 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) step 1 of this example 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-80fc0ee090ac48c8835f0c7a157b34c7
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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