1H-Pyrrolo(2,3-b)pyridine → 1H,2H,3H-pyrrolo(2,3-b)pyridine

HRID 916382Notes

Reaction equation

HRID 916382 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[H][H]>C(O)C.[Ni]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 100118891H,2H,3H-pyrrolo(2,3-b)pyridineYield 79%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 7-azaindole (20.0 g, 169 mmol) in ethanol (200 ml) was treated with wet Raney Nickel (4 g, 50% water) and stirred in a hydrogen atmosphere at 5 atmospheres pressure at 95° C. over 2 days. The reaction mixture was filtered through diatomaceous earth and the filtrate evaporated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate followed by increasingly polar mixtures of methylene chloride and methanol (saturated with ammonia) to give 7-azaindoline (12.1 g, 79%).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customthe filtrate evaporated under vacuum
  3. customThe residue was purified by column chromatography
  4. washeluting with ethyl acetate
  5. temperatureby increasingly polar mixtures of methylene chloride and methanol (saturated with ammonia)

Sources & evidence

ORD record
ord-e48071cfb99847f9bac39c1b44d94668
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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