Hydrogen Peroxide → 7-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide

HRID 626731Notes

Reaction equation

HRID 626731 reaction equation
[Br:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=2)[CH:5]=[N:6][CH:7]=1.[OH:19]O>C(Cl)Cl.C[Re](=O)(=O)=O>[Br:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=2)[CH:5]=[N+:6]([O-:19])[CH:7]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 696713917-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

Product 1

HCID 696713397-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxideYield 47.4%

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (3.43 g, 10 mmol) and methyltrioxorhenium (249 mg, 1.0 mmol) in DCM (35 mL) was added hydrogen peroxide (30% aq., 1.95 mL, 20 mmol) and the resulting mixture stirred at room temperature for 18 hours. The reaction mixture was partitioned between DCM and sodium bicarbonate (sat. aq.). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-5% methanol in DCM) to afford the title compound as a beige solid (1.7 g, 47% yield). LCMS (Method D): RT=2.46 min, m/z: 360 [M+H+].

Workup

  1. customThe reaction mixture was partitioned between DCM and sodium bicarbonate (sat. aq.)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0-5% methanol in DCM)

Sources & evidence

ORD record
ord-f10ca1ea828f44b5ba6bed3ea837fada
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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