1H-Pyrrolo[2,3-c]pyridine-4-carbonitrile → HCID 82417690, compound

HRID 2409007Notes

Reaction equation

HRID 2409007 reaction equation
[NH:1]1[C:5]2[CH:6]=[N:7][CH:8]=[C:9]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1>[Ni].N.CO>[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][C:9]([CH2:10][NH2:11])=[C:4]2[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 468357241H-Pyrrolo[2,3-c]pyridine-4-carbonitrile

Product 1

HCID 82417690HCID 82417690, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of 1H-pyrrolo[2,3-c]pyridine-4-carbonitrile (232 mg, 1.62 mmol) and Raney Ni (200 mg) in a solution of ammonia/MeOH (7N, 40 mL) was stirred at RT for 4 h. The reaction mixture was filtered and the wet cake was washed with MeOH (3×10 mL). The filtrate was concentrated under reduced pressure to afford 236 mg (99.0%) of (1H-pyrrolo[2,3-c]pyridin-4-yl)methanamine as yellow solid: MS (ESI) m/z: 148.3 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe wet cake was washed with MeOH (3×10 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f92f170c6d90423bb808618ea41049d9
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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