Potassium Iodide → Ethyl 8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine-2-carboxylate

HRID 1006690Notes

Reaction equation

HRID 1006690 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:19]=1[CH2:20]Cl.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(#N)C>[CH3:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:19]=1[CH2:20][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 22672637Ethyl 8-amino-3-methylimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 22672581Ethyl 8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine-2-carboxylateYield 56.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 8-amino-3-methylimidazo[1,2-a]pyridine-2-carboxylate (4.6 g, 21 mmol), 2,6-dimethylbenzyl chloride (3.2 g, 21 mmol), sodium carbonate (4.4 g, 42 mmol) and a cat. amount of potassium iodide were added to acetonitrile (50 ml) and refluxed for 3 h., stirred for 20 h. at room temperature and refluxed for 1 h. The solids were removed by filtration and the solvents were evaporated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride:methanol (10:1) as eluent and crystallization from ethyl acetate gave 4.0 g (56%) of the desired product.

Workup

  1. temperaturerefluxed for 3 h.
  2. temperaturerefluxed for 1 h
  3. customThe solids were removed by filtration
  4. customthe solvents were evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with water
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. customevaporated under reduced pressure
  10. customPurification of the residue by column chromatography on silica gel
  11. customcrystallization from ethyl acetate

Sources & evidence

ORD record
ord-a24f2177ff374f62bb0d8aa718521ae8
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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