1H-Pyrrolo(2,3-b)pyridine → 7-aza-1H-indole N-oxide

HRID 1964991Notes

Reaction equation

HRID 1964991 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>C(OCC)C>[NH+:1]1([O-:18])[C:9]2=[N:8][CH:7]=[CH:6][CH:5]=[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 219590977-aza-1H-indole N-oxideYield 125%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1H-pyrrolo[2,3-b]pyridine (94, 3.0 g, 25.3 mmol) dissolved in 175 ml, of diethyl ether was added m-CPBA (1.5 equiv) in portions over 30 minutes with vigorous stirring. The solution turned yellow, and precipitates formed. After two hours the solid was collected, washed with 2×50 mL of ether, and recrystallized from acetone:ether. Yield was approximately 125% due to contaminating acid. This crude material was carried through to the next step.

Workup

  1. customprecipitates
  2. customformed
  3. customAfter two hours the solid was collected
  4. washwashed with 2×50 mL of ether
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-bb4a9b1aa13e490bbda8b997e5d8a436
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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