Sodium Iodide → Ethyl 8-(2,6-Dimethylbenzylamino)-3,6-dimethylimidazo[1,2-a]pyridin-2-carboxylate

HRID 1166171Notes

Reaction equation

HRID 1166171 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([CH3:17])=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21][NH:1][C:2]1[C:3]2[N:4]([C:9]([CH3:17])=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 22997462Ethyl 8-Amino-3,6-dimethylimidazo[1,2-a]pyridin-2-carboxylate

Product 1

HCID 22997466Ethyl 8-(2,6-Dimethylbenzylamino)-3,6-dimethylimidazo[1,2-a]pyridin-2-carboxylateYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 8-amino-3,6-dimethylimidazo[1,2-a]pyridin-2-carboxylate (1.3 g, 5.6 mmol), 2,6-dimethylbenzyl chloride (0.9 g, 6.2 mmol), potassium carbonate (1.5 g, 11 mmol) and sodium iodide (0.1 g, 0.6 mmol) were added to acetonitrile (15 ml) and refluxed for 20 h. The solvent was evaporated under reduced pressure. The residue was dissolved in methylene chloride , washed twice with water and the organic layer was separated dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using heptane:ethyl acetate (2:1) as eluent gave 0.9 g (47%) of the title compound as an oil.

Workup

  1. temperaturerefluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed twice with water
  5. customthe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-8532f34b556b4cfda8b41e11893ad865
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

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