Sodium Hydroxide → 6-Bromo-7-azaindole

HRID 1749806Notes

Reaction equation

HRID 1749806 reaction equation
C([N:9]1[C:13]2=[N:14][C:15]([Br:18])=[CH:16][CH:17]=[C:12]2[CH:11]=[CH:10]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[Br:18][C:15]1[N:14]=[C:13]2[NH:9][CH:10]=[CH:11][C:12]2=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 150138931-Benzoyl-6-bromo-7-azaindole

Product 1

HCID 111599156-Bromo-7-azaindoleYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-benzoyl-6-bromo-1H-pyrrolo[2,3-b]pyridine (0.046 g, 0.15 mmol) in methanol (5.0 mL) was added with 5 N aqueous sodium hydroxide (1.0 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, the residue was extracted with diethyl ether, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 6-bromo-1H-pyrrolo[2,3-b]pyridine (0.028 g, 95%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with diethyl ether
  3. washthe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fcaa67e39a4f4393b407b84726845077
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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