Potassium Iodide → Tert-butyl [3-(2-methyl-2-nitropropyl)imidazo[1,2-a]pyridin-8-yloxy)-acetate

HRID 1790059Notes

Reaction equation

HRID 1790059 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][CH:11]=[C:12]([OH:13])[C:7]2=[N:6][CH:5]=1.Cl[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[C:23]([O:22][C:20](=[O:21])[CH2:19][O:13][C:12]1[C:7]2[N:8]([C:4]([CH2:3][C:2]([CH3:1])([N+:15]([O-:17])=[O:16])[CH3:14])=[CH:5][N:6]=2)[CH:9]=[CH:10][CH:11]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetateHCID 179554923-(2-Methyl-2-nitropropyl)imidazo[1,2-a]pyridin-8-ol

Product 1

HCID 86596187Tert-butyl [3-(2-methyl-2-nitropropyl)imidazo[1,2-a]pyridin-8-yloxy)-acetateYield 81%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-(2-Methyl-2-nitropropyl)imidazo[1,2-a]pyridin-8-ol (1.0 g, 4.25 mmol), tert-butyl chloroacetate (964 mg, 6.4 mmol), potassium carbonate (590 mg, 4.27 mmol), and a small amount of potassium iodide in 2-butanone (30 ml) are reacted as described in Amine 9. The crude product residue is chromatographed on silica gel with dichloromethane/ethanol 9:1 to give 1.2 g of tert-butyl[3-(2-methyl-2-nitropropyl)imidazo[1,2-a]pyridin-8-yloxy]-acetate (81%).

Workup

  1. customThe crude product residue is chromatographed on silica gel with dichloromethane/ethanol 9:1

Sources & evidence

ORD record
ord-3d7616d7c81644f786373d7d2a90de23
Source dataset
uspto-grants-2006_07
Patent number
US07071208B2

Reaction notes

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