m-Chloroperbenzoic acid → HCID 178422841, compound

HRID 872042Notes

Reaction equation

HRID 872042 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[N:18]=[C:17]2[NH:19][CH:20]=[CH:21][C:16]2=[CH:15][CH:14]=1>C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>[CH3:12][C:13]1[N+:18]([O-:9])=[C:17]2[NH:19][CH:20]=[CH:21][C:16]2=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 114577166-Methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178422841HCID 178422841, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 11430Potassium CarbonateSolvent

Procedure

65% m-Chloroperbenzoic acid (1374 mg) was added to a solution of 6-methyl-1H-pyrrolo[2,3-b]pyridine (570 mg) in ethyl acetate (20 ml) under ice-cooling and the mixture was stirred at room temperature for 20 minutes. After concentration of the reaction mixture in vacuo, the resulted residue was diluted with 2% aqueous solution of potassium carbonate and extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a NH-silica gel column chromatography (eluting solvent: chloroform/methanol=30/1 to 9/1) to give 6-methyl-1H-pyrrolo[2,3-b]pyridin-7-oxide (575 mg) as a colorless powder.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulted residue was purified with a NH-silica gel column chromatography (eluting solvent: chloroform/methanol=30/1 to 9/1)

Sources & evidence

ORD record
ord-78e521754ff64888ac0b1ac6680e5286
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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