Ethyl cyanoacetate → (6-Bromo-1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrile

HRID 1986367Notes

Reaction equation

HRID 1986367 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1.[C:16]([CH2:18][C:19](OCC)=O)#[N:17]>>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:19]([CH2:18][C:16]#[N:17])[N:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 860451276-bromo-N4-phenylpyridine-3,4-diamine

Product 1

HCID 86045130(6-Bromo-1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrileYield 35%

Procedure

The product from Step 4 (2.1 g, 7.95 mmol) and ethyl cyanoacetate (3.6 g, 31 mmol) were heated together at 195° C. in a sealed tube for 54 minutes. After cooling to room temperature, the product crystallized and the crystals were collected and washed with ethanol to give the title compound (0.87 g, 35%). MS (ES+) m/e 313/315 [M+H]+.

Workup

  1. customthe product crystallized
  2. customthe crystals were collected
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-65edebe5e52b49d0b25d5a482dded18f
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

Loading…