m-Chloroperbenzoic acid → HCID 178526243, compound

HRID 2120696Notes

Reaction equation

HRID 2120696 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-346c7a47c0c54b8ead48146793307ba8
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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