m-Chloroperbenzoic acid → 1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine 5-oxide

HRID 2198127Notes

Reaction equation

HRID 2198127 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:25])C=1>ClCCl.CCOC(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][N+:13]([O-:25])=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 592783571-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 580842441-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine 5-oxide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine (0.920 g, 4.31 mmol) in dichloromethane (50 mL) was added 65% m-chloroperbenzoic acid (1.26 g, 4.75 mmol). After 2 hours, the mixture was diluted with EtOAc and water. The organic layer was washed with saturated aqueous NaHCO3, brine, dried over sodium sulfate, filter and concentrated to afford 1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine 5-oxide.

Workup

  1. washThe organic layer was washed with saturated aqueous NaHCO3, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f6f1787333e84877962fc398aebfbc05
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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