5-bromo-3-(pyridin-3-ylmethyl)-1H-indole → 5-Cyano-3-(pyridin-3-ylmethyl)-1H-indole

HRID 355985Notes

Reaction equation

HRID 355985 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[Cu](C#N)[C:19]#[N:20]>CN(C)C=O>[C:19]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)#[N:20]

Participants

4

Reactant 2

HCID 189408375-bromo-3-(pyridin-3-ylmethyl)-1H-indoleHCID 178418260HCID 178418260, compound

Product 1

HCID 189408515-Cyano-3-(pyridin-3-ylmethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound of Description 3 [5-Bromo-3-(pyridin-3-ylmethyl)-1H-indole] (1.1 g; 0.0038 mol) and copper cyanide (0.86 g; 0.0096 mol) in dimethylformamide (35 ml) was treated at 140° C. for 8 hours. The reaction mixture was poured into an ice ammonium hydroxide solution and the product was extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol (97/3), the desired compound was obtained.

Workup

  1. additionwas treated at 140° C. for 8 hours
  2. extractionthe product was extracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. customevaporated under vacuum
  6. customAfter purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol (97/3)

Sources & evidence

ORD record
ord-15c592396a66413e8993383cf5f6196f
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Reaction notes

Loading…