Trifluoroacetic anhydride → 7-(Benzyloxy)-[1,2,4]triazolo[1,5-a]pyridine

HRID 240583Notes

Reaction equation

HRID 240583 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24](/[N:28]=[CH:29]\[NH:30]O)[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][N:25]2[N:30]=[CH:29][N:28]=[C:24]2[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 178526368HCID 178526368, compound

Product 1

HCID 669371067-(Benzyloxy)-[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic anhydride (2.62 mL, 18.9 mmol) was added dropwise to a solution of (Z)-N′-(4-(benzyloxy)pyridin-2-yl)-N-hydroxyformamidine (4.37 g, 17.9 mmol) in THF (180 mL), and the mixture was cooled to 0° C. The ice bath was then removed and the reaction was stirred for 12 hours. The reaction was concentrated to about 15-25 mL, then poured into 400 mL of iced 1 M NaOH. The mixture was stirred for 1 hour. The resulting white solids were collected by filtration, washed with hexanes, and dried under high vacuum for 1 hour to provide the desired product.

Workup

  1. customThe ice bath was then removed
  2. concentrationThe reaction was concentrated to about 15-25 mL
  3. additionpoured into 400 mL of iced 1 M NaOH
  4. stirringThe mixture was stirred for 1 hour
  5. filtrationThe resulting white solids were collected by filtration
  6. washwashed with hexanes
  7. customdried under high vacuum for 1 hour

Sources & evidence

ORD record
ord-78a748461afe482eb8b15c8e274cc96e
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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