Sodium Iodide → 2,3-Dimethyl-8-(2-ethyl-6-methylbenzyloxy)imidazo[1,2-a]pyridine

HRID 1386078Notes

Reaction equation

HRID 1386078 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]2[C:11]=1[CH3:12].[CH2:13]([C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:16]=1[CH2:17]Cl)[CH3:14].[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:17][C:16]3[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:15]=3[CH2:13][CH3:14])=[CH:8][CH:7]=[CH:6][N:5]2[C:11]=1[CH3:12]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 121489182-Ethyl-6-methylbenzyl chlorideHCID 224679492,3-Dimethylimidazo[1,2-a]pyridin-8-ol

Product 1

HCID 217173522,3-Dimethyl-8-(2-ethyl-6-methylbenzyloxy)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,3-Dimethyl-8-hydroxyimidazo[1,2-a]pyridine (0.8 g, 5 mmol), 2-ethyl-6-methylbenzyl chloride, sodium iodide (0.25 g, 1.7 mmol) and sodium carbonate (1.2 g, 11 mmol) were added to acetone (40 ml) and the mixture was refluxed for 5 h. The acetone was evaporated and the residue was solved in methylene chloride and washed with water. The organic solvent was dried and was evaporated under reduced pressure. The residue was purified twice by column chromatography on silica gel using (a) methylene chloride: ethylacetate(1:2), (b) methylene chloride:ethylacetate(2:1), as eluent to give the title compound. (0.02 g, 1.4%)

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. customThe acetone was evaporated
  3. washwashed with water
  4. customThe organic solvent was dried
  5. customwas evaporated under reduced pressure
  6. customThe residue was purified twice by column chromatography on silica gel using (a) methylene chloride: ethylacetate(1:2), (b) methylene chloride:ethylacetate(2:1), as eluent

Sources & evidence

ORD record
ord-6aff95fb3e074e4e861282946aa76817
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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