6-Fluoro-1H-indole-4-carbonitrile → HCID 71699932, compound

HRID 475265Notes

Reaction equation

HRID 475265 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5]2[CH:6]=[CH:7][NH:8][C:9]=2[CH:10]=1>N.CO.[Ni]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([CH2:11][NH2:12])[CH:3]=1

Participants

5

Reactant 1

HCID 533994126-Fluoro-1H-indole-4-carbonitrile

Product 1

HCID 71699932HCID 71699932, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of 226 (588 mg, 3.68 mmol) in 7N NH3 in MeOH (20 mL) was added Raney nickel (20 mg), and then the reaction was stirred under hydrogen (1 atm.) at RT overnight. The dark mixture was filtered and the filtrate was concentrated in vacuo to afford 500 mg (85%) of (6-fluoro-1H-indol-4-yl)methanamine (228) as white solid: MS (ESI) m/z=148.1 [M−16]+.

Workup

  1. filtrationThe dark mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-550e19c3b722438d90e46839d6b385e5
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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