Potassium Carbonate → 2-methyl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid

HRID 1639826Notes

Reaction equation

HRID 1639826 reaction equation
I[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[C:12](=O)([O-:14])[O-:13].[K+].[K+]>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:11][C:9]1[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:12]([OH:14])=[O:13])[N:7]2[N:8]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 59334570HCID 59334570, compound

Product 1

HCID 594519082-methyl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-iodo-2-methyl[1,2,4]triazolo[1,5-a]pyridine (13.5 g, 52.1 mmol) in methanol (521 mL) were added palladium acetate (1.17 g, 5.21 mmol), potassium carbonate (21.6 g, 156 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (2.15 g, 5.21 mmol), and the mixture was stirred under carbon monoxide atmosphere at 2 atm at room temperature for 1 hr. The mixture was warmed to 50° C. and stirred for 12 hr. The reaction mixture was filtered through celite. The solvent was evaporated under reduced pressure. The residue was dissolved in water (300 mL), washed with chloroform, and 2 M hydrochloric acid was added to adjust the solution to pH 2. The aqueous layer was evaporated under reduced pressure, the residue was dissolved in methanol, and insoluble material was filtered off. The solvent was evaporated under reduced pressure to give 2-methyl[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid as a crudely purified product.

Workup

  1. temperatureThe mixture was warmed to 50° C.
  2. stirringstirred for 12 hr
  3. filtrationThe reaction mixture was filtered through celite
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in water (300 mL)
  6. washwashed with chloroform, and 2 M hydrochloric acid
  7. additionwas added
  8. customThe aqueous layer was evaporated under reduced pressure
  9. dissolutionthe residue was dissolved in methanol
  10. filtrationinsoluble material was filtered off
  11. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b7aeac58c7f3410b8bb9bab416d77376
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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