1H-Pyrrolo(2,3-b)pyridine → HCID 178524353, compound

HRID 240466Notes

Reaction equation

HRID 240466 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16]O)=[O:15]>COCCOC.CCCCCCC>[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([OH:16])=[O:15].[N+:1]1([O-:15])[CH:2]=[CH:3][C:4]2[C:9]=1[NH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

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

Product 1

HCID 178524353HCID 178524353, compoundYield 162.3%

Reagents, catalysts & solvents 1

HCID 86630134HCID 86630134, compoundSolvent

Procedure

To a solution of 7-azaindole (Int-5, 23.6 g, 200 mmol) in DME/heptane (1:2, 300 mL) was added 3-chloroperoxybenzoic acid (85 wt %, 44.7 g, 220 mmol) portion-wise. The slurry was stirred at room temperature for 3 h. The precipitate was collected by filtration and washed with heptane (100 mL). After dried, 51.9 g of 7-azaindole N-oxide 3-chlorobenzoate was obtained (51.9 g, 89%). mp 140-143° C.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with heptane (100 mL)
  3. customAfter dried

Sources & evidence

ORD record
ord-d9f79bff15e54583a04060d682620b62
Source dataset
uspto-grants-2014_02
Patent number
US08648086B2

Reaction notes

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