Benzyl 2-(3-methyl[1,2,4]triazolo[4,3-a]pyridin-8-yl)acrylate → 2-(3-Methyl[1,2,4]triazolo[4,3-a]pyridin-8-yl)propanoic acid

HRID 1888198Notes

Reaction equation

HRID 1888198 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11](=[CH2:22])[C:12]([O:14]CC3C=CC=CC=3)=[O:13])[C:5]2=[N:4][N:3]=1>[Pd].CO>[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]([CH3:22])[C:12]([OH:14])=[O:13])[C:5]2=[N:4][N:3]=1

Participants

4

Reactant 1

HCID 66924470Benzyl 2-(3-methyl[1,2,4]triazolo[4,3-a]pyridin-8-yl)acrylate

Product 1

HCID 579075822-(3-Methyl[1,2,4]triazolo[4,3-a]pyridin-8-yl)propanoic acidYield 77.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 0.040 mg (0.038 mmol) of 10% palladium on carbon was added a solution of (0.080 g, 0.27 mmol) of benzyl 2-(3-methyl[1,2,4]triazolo[4,3-a]pyridin-8-yl)acrylate prepared in Step C above in 4 mL of methanol. The resulting suspension was stirred under an atmosphere of hydrogen (1 atmosphere) for 6 h. The residue was filtered through a pad of Celite® and the pad was washed cold methanol. The combined filtrates were evaporated under reduced pressure to give yield the title compound (0.043 g, 77%). LC-MS: iniz (ES) 206 (MH)+.

Workup

  1. filtrationThe residue was filtered through a pad of Celite®
  2. washthe pad was washed cold methanol
  3. customThe combined filtrates were evaporated under reduced pressure
  4. customto give

Sources & evidence

ORD record
ord-b750d7b270114cdb82fef269e71314d1
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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