1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole → 1-(3-Cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazole

HRID 1581658Notes

Reaction equation

HRID 1581658 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:14]([CH2:15][OH:16])=[CH:13][C:12]([C:17]([F:20])([F:19])[F:18])=[N:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].I([O-])(=O)(=O)=[O:22].[Na+]>C(#N)C.O.[Ru](Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:14]([C:15]([OH:22])=[O:16])=[CH:13][C:12]([C:17]([F:19])([F:20])[F:18])=[N:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

6

Reactant 2

HCID 222807401-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazoleHCID 23667635Sodium periodate

Product 1

HCID 104700071-(3-Cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazoleYield 57.1%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(3-cyano-4-fluoro-phenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole (0.45 g, 1.58 mmol) in acetonitrile (10 mL) was added catalytic amount of ruthenium chloride at 0° C. followed by addition of a solution of sodium periodate (0.71 g, 3.32 mmol) in water. The reaction was stirred at 0° C. to room temperature overnight. The next day the acetonitrile was evaporated and the residue was partitioned between ethyl acetate and water, washed with brine, dried over sodium sulfate, filtered and concentrated to give 1-(3-cyano-4-fluoro-phenyl)-3-trifluoromethyl-5-hydroxycarbonylpyrazole (0.27 g, 57% yield) as pure compound: MS (ES−): 298 (M—H)− (40%).

Workup

  1. customThe next day the acetonitrile was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6665309fd40c48409bb08163b5cf7510
Source dataset
uspto-grants-2004_05
Patent number
US06730689B2

Reaction notes

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