Trifluoroacetic acid → 4-([1,2,4]Triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoic acid

HRID 240587Notes

Reaction equation

HRID 240587 reaction equation
[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([F:24])[C:12]=3[Cl:25])=[CH:6][C:5]=12.FC(F)(F)C(O)=O>ClCCl>[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:23]=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:24])[C:12]=3[Cl:25])=[CH:6][C:5]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66937100Tert-butyl 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoate

Product 1

HCID 669372644-([1,2,4]Triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 25 ml flask was charged with tert-butyl 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoate (0.060 g, 0.16 mmol) and dichloromethane (1.6 ml). The reaction was cooled to 0° C., and 2,2,2-trifluoroacetic acid (0.50 ml, 0.16 mmol) was added. The reaction was stirred for 20 minutes, then warmed to ambient temperature, stirred an additional 3 hours, and then concentrated to provide the desired product as a colorless oily residue.

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred an additional 3 hours
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-71a23a64da1143f1900d1e38a7096dce
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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