1-Methyl-1H-pyrrolo[2,3-B]pyridine-5-carbonitrile → HCID 66837868, compound

HRID 73117Notes

Reaction equation

HRID 73117 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]#[N:12])[CH:10]=[C:5]2[CH:4]=[CH:3]1>N.CO.[Ni]>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([CH2:11][NH2:12])[CH:10]=[C:5]2[CH:4]=[CH:3]1

Participants

4

Reactant 1

HCID 497588931-Methyl-1H-pyrrolo[2,3-B]pyridine-5-carbonitrile

Product 1

HCID 66837868HCID 66837868, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a stirred solution of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (210 mg, 1.3 mmol) in 10% NH3-MeOH (10 mL) was added Raney Nickel (0.5 mL, Raney (registered trademark) 2800 slurry in water), and the mixture was stirred at room temperature under hydrogen atmosphere for 4 hrs. The mixture was filtered through a pad of Celite (registered trademark), washed with MeOH, the filtrate was concentrated to give 200 mg (93% yield) of the titled compound as a white solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite (registered trademark)
  2. washwashed with MeOH
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5d5178c71a1742998c0418d7869aba8b
Source dataset
uspto-grants-2014_09
Patent number
US08829026B2

Reaction notes

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