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

HRID 2184303Notes

Reaction equation

HRID 2184303 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.[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>[CH3:15][C:13]1[N:14]=[C:3]2[C:2]([NH:1][CH2:20][C:19]3[C:22]([CH3:26])=[CH:23][CH:24]=[CH:25][C:18]=3[CH3:17])=[CH:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][N:4]2[C:12]=1[CH3:16]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 9855934Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 12148917Methyl 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylateYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate (0.8 g, 3.6 mmol), 2,6-dimethylbenzylchloride (0.57 g, 3.7 mmol), sodium carbonate (1.0 g, 9.4 mmol) and a catalytic amount of potassium iodide were added to acetonitrile (10 ml) and were refluxed for 20 h. Following filtration, the salts were washed with methylene chloride and the solvents were evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride: ethyl acetate (75:25) as eluent. The yellow residue was treated with hexane to give 0.23 g (19%) of the title product.

Workup

  1. temperaturewere refluxed for 20 h
  2. filtrationfiltration
  3. washthe salts were washed with methylene chloride
  4. customthe solvents were evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. additionThe yellow residue was treated with hexane

Sources & evidence

ORD record
ord-8070a1fda11944f288fdfa064471510c
Source dataset
uspto-grants-2005_05
Patent number
US06900324B2

Reaction notes

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