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

HRID 908225Notes

Reaction equation

HRID 908225 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. Upon cooling, water (4 ml) was added and the precipitate was filtered and dried under vacuum to give a first crop of the desired product. The filtrate was evaporated, the residue was taken up in ethyl acetate (20 ml) and washed (water, brine). The organic layer was dried (Na2SO4) and evaporated. The residue was purified by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50) to give a second crop of the desired product. The combined crops gave the title compound (350 mg, 40%). MS (m/e)=235.1 [M+H+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureUpon cooling
  4. filtrationthe precipitate was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1b7aa5b3f3c44169abc636b7dae54798
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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