Potassium Iodide → 3-Carboethoxy-8-(2-ethyl-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 1386099Notes

Reaction equation

HRID 1386099 reaction equation
[C:1]([C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([OH:15])[C:9]2=[N:8][C:7]=1[CH3:16])([O:3][CH2:4][CH3:5])=[O:2].[CH2:17]([C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21]Cl)[CH3:18].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(#N)C>[C:1]([C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH2:21][C:20]3[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:19]=3[CH2:17][CH3:18])[C:9]2=[N:8][C:7]=1[CH3:16])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 121489182-Ethyl-6-methylbenzyl chlorideHCID 21717316Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 217173563-Carboethoxy-8-(2-ethyl-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridineYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 3-carboethoxy-8-hydroxy-2-methylimidazo[1,2-a]pyridine (0.92 g, 4.2 mmol), (0.7 g, 4.2 mmol) 2-ethyl-6-methylbenzylchloride (0.7 g, 4.2 mmol), sodium carbonate (1.0 g, 9.4 mmol) and a catalytic amount of potassium iodide in acetonitrile (40 ml) was refluxed for 4 h. After filtration and evaporation of the solvent under reduced pressure the residue was purified by column chromatography on silica gel using methylene chloride:ethylacetate as eluent to give 1.0 g, (68%) of the title compound.

Workup

  1. filtrationAfter filtration and evaporation of the solvent under reduced pressure the residue
  2. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-331a24fd443f4862a9a0f3a0d33ff252
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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