Potassium Iodide → Methyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate

HRID 427500Notes

Reaction equation

HRID 427500 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.[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-].[K+].[K+].[I-].[K+]>C(Cl)Cl.C(#N)C>[CH3:15][C:13]1[N:14]=[C:3]2[C:2]([NH:1][CH2:21][C:20]3[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:19]=3[CH2:17][CH3:18])=[CH:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][N:4]2[C:12]=1[CH3:16]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 9855934Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylateHCID 121489182-Ethyl-6-methylbenzyl chloride

Product 1

HCID 18357442Methyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylateYield 38%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate (0.7 g, 3.2 mmol), 2-ethyl-6-methylbenzylchloride (0.54 g, 3.2 mmol), potassium carbonate (0.9 g, 6.4 mmol) and a cat. amount of potassium iodide were added to acetonitrile (20 ml) and were refluxed for 6 h. Following filtration, the acetonitrile was evaporated under reduced pressure to give an oil. The oily residue was solved in methylene chloride and washed with water. The organic layer was separated, dried over Na2SO4 and evaporated under reduced pressure to give a solid. Purification by column chromatography on silica gel using methylene chloride:ethylacetate (10:1) as eluent gave 0.42 g (38%) of the title compound.

Workup

  1. temperaturewere refluxed for 6 h
  2. filtrationfiltration
  3. customthe acetonitrile was evaporated under reduced pressure
  4. customto give an oil
  5. washwashed with water
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. customevaporated under reduced pressure
  9. customto give a solid
  10. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-13c20cc0099640b8a5ffee934be0148a
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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