Potassium Iodide → 2-[3-(2-Methyl-2-nitropropyl)imidazo[1,2-a]pyridin-7-yloxy]-acetamide

HRID 852219

Reaction equation

HRID 852219 reaction equation
[CH3:1][C:2]([N+:15]([O-:17])=[O:16])([CH3:14])[CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][C:11]([OH:13])=[CH:12][C:7]2=[N:6][CH:5]=1.Cl[CH2:19][C:20]([NH2:22])=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[CH3:14][C:2]([N+:15]([O-:17])=[O:16])([CH3:1])[CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][C:11]([O:13][CH2:19][C:20]([NH2:22])=[O:21])=[CH:12][C:7]2=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 178441236HCID 178441236, compound

Product 1

HCID 220385692-[3-(2-Methyl-2-nitropropyl)imidazo[1,2-a]pyridin-7-yloxy]-acetamideYield 34.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-(2-Methyl-2-nitropropyl)imidazo[1,2-a]pyridin-7-ol (1.5 g, 6.38 mmol), chloroacetamide (1.19 g, 12.73 mmol), potassium carbonate (6.4 mmol) and a small amount of potassium iodide in 2-butanone (30 ml) is heated at reflux overnight. The solids are removed by filtration and the filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel with dichloromethane/methanol 3:1 to 1:1 to give 640 mg of 2-[3-(2-methyl-2-nitropropyl)imidazo[1,2-a]pyridin-7-yloxy]-acetamide (34%).

Workup

  1. temperatureat reflux overnight
  2. customThe solids are removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is chromatographed on silica gel with dichloromethane/methanol 3:1 to 1:1

Sources & evidence

ORD record
ord-5c849ac6426645c392d44416bed12283
Source dataset
uspto-grants-2007_08
Patent number
US07253181B2

Linked notes

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