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

HRID 2068026Notes

Reaction equation

HRID 2068026 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 The residue
  3. customwas 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-4bd497eaa983440db7cb9c66db3068fa
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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