HCID 86689864, compound → HCID 86689866, compound

HRID 2409056Notes

Reaction equation

HRID 2409056 reaction equation
[CH3:1][Si:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[CH:12]=[N:13][CH:14]=[C:15]([C:16]#[N:17])[C:10]=2[CH:9]=[CH:8]1>[Ni].N.CO>[CH3:1][Si:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2=[CH:12][N:13]=[CH:14][C:15]([CH2:16][NH2:17])=[C:10]2[CH:9]=[CH:8]1

Participants

4

Reactant 1

HCID 86689864HCID 86689864, compound

Product 1

HCID 86689866HCID 86689866, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a solution of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-4-carbonitrile (683 mg, 2.5 mmol) in a solution of NH3/MeOH (7 N, 20 mL) was added Raney nickel (300 mg). The mixture was stirred under hydrogen for 3 h. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to afford 673 mg (97.1%) of (1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methanamine as a yellow oil. MS (ESI): m/z=278.1 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-7aa97baf27e44d7195dfe5847c22c618
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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