Water → 7-Amino-2-phenylimidazo[1,2-A]pyridine-6-carbonitrile

HRID 2382730Notes

Reaction equation

HRID 2382730 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.C([O-])(O)=O.[Na+].[C:16]([C:18]1[CH:19]=[N:20][C:21]([NH2:25])=[CH:22][C:23]=1[NH2:24])#[N:17].O>CO>[NH2:24][C:23]1[C:18]([C:16]#[N:17])=[CH:19][N:20]2[CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:25]=[C:21]2[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 2958964,6-DiaminonicotinonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 670415967-Amino-2-phenylimidazo[1,2-A]pyridine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromoacetophenone (1.11 g, 5.6 mmol) and NaHCO3 (470 mg) were added to a solution of 3-cyano-4,6-diaminopyridine (500 mg, 3.7 mmol) in methanol (7.5 ml), and the mixture was heated to reflux overnight. The mixture was cooled, water (4 ml) was added, and the precipitate was filtered to give a first crop of the desired product. The filtrate was evaporated, taken up in ethyl acetate and washed (water, brine). The organic layer was dried (Na2SO4), evaporated, and the residue was purified by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40) to yield a second crop of product. The combined isolates were dried to give the title compound (350 mg, 40%). MS (m/e)=235.1 [M+H+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThe mixture was cooled
  4. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-a007331f122d4e1ab11061ba87240ce1
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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