5-Bromo-2,3-dihydro-7-azaindole → 5-bromo-1H-pyrrolo[2,3-b]pyridine

HRID 2068028Notes

Reaction equation

HRID 2068028 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 219640795-Bromo-2,3-dihydro-7-azaindole

Product 1

HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineYield 78.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 5-bromo-7-azaindoline (15.6 g, 78 mmol) and precipitated, active manganese (IV) oxide (21.9 g, 252 mmol) in toluene (300 mls) was heated at 90° C. for 1 hour and the hot solution filtered through a pad of diatomaceous earth. The diatomaceous earth and manganese residues were washed with acetone and these washings added to the toluene filtrate. Evaporation of the filtrate under vacuum gave 5-bromo-7-azaindole (12.1 g, 78%).

Workup

  1. customprecipitated
  2. filtrationthe hot solution filtered through a pad of diatomaceous earth
  3. washThe diatomaceous earth and manganese residues were washed with acetone
  4. additionthese washings added to the toluene filtrate
  5. customEvaporation of the filtrate under vacuum

Sources & evidence

ORD record
ord-18bc1fa341e14ec598a7d297e23c4bee
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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