7-Chloro-1H-pyrrolo[2,3-c]pyridine → 6-Azaindole

HRID 1869210Notes

Reaction equation

HRID 1869210 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12>CCO.[Pd]>[NH:8]1[C:7]2=[CH:2][N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9]1

Participants

4

Reactant 1

HCID 114350487-Chloro-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 92196-AzaindoleYield 76.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 7-chloro-1H-pyrrolo[2,3-c]pyridine (650 mg, 4.2 mmol) and Pd/C (10%, 50 mg) in EtOH (25 mL) was stirred at RT under H2 atmosphere (balloon pressure). The reaction mixture was filtered through a celite pad, and the filter cake was washed with EtOAc (10 mL). The filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH, 9/1/0.1), affording 1H-Pyrrolo[2,3-c]pyridine as a white solid (380 mg, 75% yield).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washthe filter cake was washed with EtOAc (10 mL)
  3. concentrationThe filtrate was concentrated
  4. custompurified via flash chromatography (DCM/MeOH/NH4OH, 9/1/0.1)

Sources & evidence

ORD record
ord-4a49db06813c406386c9e8da701dfbd6
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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