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

HRID 626711Notes

Reaction equation

HRID 626711 reaction equation
[Cl: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.O=[Mn]=O>[Cl: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

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 696714387-Chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

Product 1

HCID 696716927-Chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxideYield 89%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (2.7 g, 9.0 mmol) and methyltrioxorhenium (31 mg, 0.09 mmol) in DCM (6 mL) was added hydrogen peroxide (30% aq., 1.75 mL, 18.0 mmol) and the resulting mixture stirred at room temperature for 18 hours. A catalytic amount of MnO2 was added to the mixture and stirring was continued for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was triturated in toluene to afford the title compound as a beige solid (2.5 g, 89% yield). LCMS (Method D): RT=2.57 min, m/z: 314 [M+H+].

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was triturated in toluene

Sources & evidence

ORD record
ord-37b6a6f2f8fc41b5882ba09611e0de6b
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

Loading…