Water → 4-(3-(Trifluoromethyl)pyridin-2-YL)benzoic acid

HRID 1391426Notes

Reaction equation

HRID 1391426 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].O.[C:19](#N)[CH3:20]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([C:20]2[CH:19]=[CH:7][C:6]([C:12]([OH:13])=[O:15])=[CH:5][CH:4]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

Product 1

HCID 534262354-(3-(Trifluoromethyl)pyridin-2-YL)benzoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
160 °C

Procedure

4-Bis(hydroxyl)boron-1-methylbenzoate (2.8 mmol) was dissolved in acetonitrile (2 ml) and added to a 5 ml microwave vessel. To the solution was 3.5 mmol of 2-chloro-3-trifluoromethylpyridine (633 mg), 34 mg of tetrakis(triphenylphosphine)-palladium(0). After stirring until dissolution, 8.4 mmol of potassium carbonate (1.16 g) was added, followed by 1 ml of water. The mixture was then heated at 160° C. for 300 seconds. After reaction completion, the solvents were evaporated under vacuum. The residue was dissolved in 2N KOH and THF and heated for 10 min. After hydrolysis, the THF was evaporated and the basic layer was washed with EtOAC. The aqueous layer was then acidified and extracted 3 times with EtOAc. The organic layers were combined and washed with water and brine. After drying, filtration and evaporation, the residue was prufied by HPLC to give of the target compound as a white solid (602 mg; 81%).

Workup

  1. additionadded to a 5 ml microwave vessel
  2. additionwas added
  3. customAfter reaction completion
  4. customthe solvents were evaporated under vacuum
  5. dissolutionThe residue was dissolved in 2N KOH
  6. temperatureTHF and heated for 10 min
  7. customAfter hydrolysis
  8. customthe THF was evaporated
  9. washthe basic layer was washed with EtOAC
  10. extractionextracted 3 times with EtOAc
  11. washwashed with water and brine
  12. customAfter drying
  13. filtrationfiltration and evaporation

Sources & evidence

ORD record
ord-bf01f8c01679416abdc35f0a9cbe5046
Source dataset
uspto-grants-2008_03
Patent number
US07338950B2

Reaction notes

Loading…