1H-Pyrrolo(2,3-b)pyridine → HCID 178526243, compound

HRID 878994Notes

Reaction equation

HRID 878994 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.ClC1C=CC=C(C(OO)=[O:18])C=1>COCCOC>[NH:1]1[C:5]2=[N+:6]([O-:18])[CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 178526243HCID 178526243, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1H-pyrrolo[2,3-b]pyridine (495 mg) in 1,2-dimethoxyethane (20 mL) was added 3-chloroperbenzoic acid (1.48 g) at room temperature, and then the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with water, and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (360 mg) as a white solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with chloroform
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e3b64cad5813415085d8fb3725489f88
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

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