Sodium Thiosulfate → 2-(2,6-Dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5-oxide

HRID 626722Notes

Reaction equation

HRID 626722 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH:18]=[C:12]2[CH:13]=[N:14][CH:15]=[C:16]([F:17])[C:11]2=[N:10]1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH:18]=[C:12]2[CH:13]=[N+:14]([O-:27])[CH:15]=[C:16]([F:17])[C:11]2=[N:10]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 696718462-(2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

Product 1

HCID 696712512-(2,6-Dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5-oxideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 2-(2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine (5.4 g, 19.1 mmol) in DCM (100 mL) was added mCPBA (5.2 g, 30.0 mmol). The reaction mixture was stirred for 1.5 hours, warmed to room temperature, and stirred for a further 16 hours. Sodium thiosulfate (sat. aq.) was added and the layers were partitioned. The organic layer was washed with sodium hydrogen carbonate (sat. aq.) and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was triturated with ether to afford the title compound as a beige solid (5.04 g, 89% yield). LCMS (Method C): RT=2.45 min, m/z: 298 [M+H+].

Workup

  1. stirringstirred for a further 16 hours
  2. customthe layers were partitioned
  3. washThe organic layer was washed with sodium hydrogen carbonate (sat. aq.) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-4b52b5e051f740bd804f370b0b4268c5
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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