1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazole → 1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-pyrazole-5-carboxylic acid

HRID 394816Notes

Reaction equation

HRID 394816 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[O:15]C=CC=3)=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]([C:24]([F:27])([F:26])[F:25])=[N:10]2)=[CH:5][CH:4]=1.C(Cl)(Cl)(Cl)Cl.C(#N)C.O.I([O-])(=O)(=O)=[O:38].[Na+]>O.[Ru](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([OH:15])=[O:38])=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]([C:24]([F:26])([F:25])[F:27])=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 179399581-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazoleHCID 22592919water acetonitrile CCl4HCID 23667635Sodium periodate

Product 1

HCID 179399451-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-pyrazole-5-carboxylic acidYield 53.1%

Reagents, catalysts & solvents 1

HCID 6093376Ruthenium trichloride hydrateCatalyst

Procedure

To a solution of 1-[(4-methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazole (1.0 g, 2.63 mmol) in 4:4:6 carbon tetrachloride/acetonitrile/water was added sodium periodate (2.5 g, 11.8 mmol) and ruthenium (III) chloride monohydrate (11 mg, 0.05 mmol). The resulting biphasic reaction was stirred vigorously at ambient temperature for 24 h. The reaction was quenched with 10% aq HCl and diluted with ethyl acetate. The organics were washed with brine, dried (MgSO4), filtered through a pad of Celite and concentrated. The residue was dissolved in 1:1 hexanes/ethyl acetate and extracted with sat'd aq Na2CO3 (2 times). The combined aqueous extracts were acidified and extracted with ethyl acetate. The ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated to afford 0.5 g (53%) of the title compound as a solid. LRMS (ES−): 357.0 (M−H)−.

Workup

  1. customThe resulting biphasic reaction
  2. customThe reaction was quenched with 10% aq HCl
  3. additiondiluted with ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through a pad of Celite
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in 1:1 hexanes/ethyl acetate
  9. extractionextracted with sat'd aq Na2CO3 (2 times)
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate extracts were washed with brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-a7daa4949a304f8e97f8f1eda67a8549
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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