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

HRID 914947Notes

Reaction equation

HRID 914947 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-a1b4c7f4ff6a48708d2d3c2d2281fe64
Source dataset
uspto-grants-2007_09
Patent number
US07265127B2

Reaction notes

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