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

HRID 1994203Notes

Reaction equation

HRID 1994203 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][C:5]2=[N:6][CH:7]=1>C(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

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

Product 1

HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineYield 100.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of azaindoline 5 (7.00 g, 35.2 mmol) in CH2Cl2 (664 mL) was added activated MnO2 (3.06 g, 35.2 mmol), and progress of the reaction was monitored by 1H NMR of reaction aliquots. After 3 days the mixture was filtered through a pad of silica, and the pad was washed with EtOAc. The filtrates were concentrated to afford the azaindole 27 (6.98 g, 100%) as a brown solid. 1H NMR data as in Method 1.

Workup

  1. customwas monitored by 1H NMR of reaction aliquots
  2. filtrationAfter 3 days the mixture was filtered through a pad of silica
  3. washthe pad was washed with EtOAc
  4. concentrationThe filtrates were concentrated

Sources & evidence

ORD record
ord-bd966f101a3c4d0f8cf6390ec813f70f
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

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