m-Chloroperbenzoic acid → HCID 178526243, compound

HRID 860086Notes

Reaction equation

HRID 860086 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3]C=1C=O.C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[NH:1]1[C:3]2=[N+:4]([O-:21])[CH:5]=[CH:6][CH:7]=[C:8]2[CH:9]=[CH:10]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 594088Quinoxaline-2-carbaldehyde

Product 1

HCID 178526243HCID 178526243, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-azaindole 22-1 (30.6 g, 259 mmol) in methylene chloride (300 mL) was treated with mCPBA (75.6 g, 285 mmol) at room temperature for 12 h. The reaction mixture was washed with saturated aqueous NaHCO3 (3×100 mL), dried (Na2SO4), filtered, and concentrated in vacuo. Silica gel chromatography (100×250 mm silica, 10% to 50% EtOAc/hexanes) afforded 23.5 g of 1H-pyrrolo[2,3-b]pyridine 7-oxide as a white solid.

Workup

  1. washThe reaction mixture was washed with saturated aqueous NaHCO3 (3×100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fd3ad18dbf44921a7dff58a96540635
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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