Acetonitrile → HCID 86729698, compound

HRID 1507639Notes

Reaction equation

HRID 1507639 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10](SC)=[N:9]2)=[CH:4][CH:3]=1.O[O:19][S:20]([O-:22])=O.[K+].[C:24](#N)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([S:20]([CH3:24])(=[O:22])=[O:19])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 23707502Potassium hydroxy sulfiteHCID 86729699HCID 86729699, compound

Product 1

HCID 86729698HCID 86729698, compound

Procedure

1-(4-fluorophenyl)-3-(methylthio)-1H-pyrazole-5-carboxylic acid (120 mg, 0.48 mmol) was dissolved in acetonitrile (5 mL) at RT. Oxone™ (440 mg, 1.4 mmol) was added. The mixture was stirred at RT for 30 min and then heated at 50° C. for 3 h. The mixture was cooled to RT and most volatiles were removed under vacuum. The residue was partitioned between DCM/brine. The DCM layer was dried over Na2SO4 and filtered. Concentration of the filtrate afforded the crude 1-(4-fluorophenyl)-3-(methylsulfonyl)-1H-pyrazole-5-carboxylic acid (−140 mg), which was used without further purification. LC-MS [M+H] 285.1.

Workup

  1. temperatureheated at 50° C. for 3 h
  2. temperatureThe mixture was cooled to RT
  3. custommost volatiles were removed under vacuum
  4. customThe residue was partitioned between DCM/brine
  5. dry with materialThe DCM layer was dried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5c6c14668848412ca3da14f9c3bc99a3
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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