HCID 86762616, compound → HCID 86762617, compound

HRID 2409044Notes

Reaction equation

HRID 2409044 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:10][C:5]2=[N:6][C:7]=1[C:8]#[N:9]>[Ni].N.CO>[F:1][C:2]1[CH:3]=[C:4]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:10][C:5]2=[N:6][C:7]=1[CH2:8][NH2:9]

Participants

4

Reactant 1

HCID 86762616HCID 86762616, compound

Product 1

HCID 86762617HCID 86762617, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a solution of 6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (1096 mg, 3.77 mmol) in a solution of NH3/MeOH (7 N, 100 mL) was added Raney nickel (1000 mg), followed by stirring under a hydrogen atmosphere overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to afford (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)methanamine (1000 mg, 90%). MS (ESI): m/z=296.1 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-6f4b3ba813ee461a94437b3cd02da21e
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

Loading…