Potassium Iodide → HCID 21717326, compound

HRID 1386067Notes

Reaction equation

HRID 1386067 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH2:6]Br)=[C:4]([CH3:11])[CH:3]=1.ClC1C=C(C)C=C(C)C=1CBr.[NH2:23][C:24]1[C:25]2[N:26]([C:30]([CH3:34])=[C:31]([CH3:33])[N:32]=2)[CH:27]=[CH:28][CH:29]=1.[I-].[K+].C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC>[CH3:33][C:31]1[N:32]=[C:25]2[C:24]([NH:23][CH2:6][C:5]3[C:8]([CH3:10])=[CH:9][C:2]([Cl:1])=[CH:3][C:4]=3[CH3:11])=[CH:29][CH:28]=[CH:27][N:26]2[C:30]=1[CH3:34]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amineHCID 22672610HCID 22672610, compoundHCID 22672639HCID 22672639, compound

Product 1

HCID 21717326HCID 21717326, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-chloro-2,6-dimethylbenzylbromide and 2-chloro-4,6-dimethylbenzylbromide (1.1 g, 4.68 mmol) and 8-amino-2,3-dimethylimidazo[1,2-a]pyridine (4.65 mmol) was dissolved in 15 ml dimethoxyethane. Potassium iodide (0.5 g, 3.0 mmol) and Na2CO3 (1 g, 9.4 mmol) was added. The mixture was refluxed for 4 hours. The solvent was evaporated and the residue was purified by column chromatography on silica gel. The product was eluted with a mixture of methylene chloride and ethyl acetate (70:30). 70 mg of the title compound was obtained.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography on silica gel
  4. washThe product was eluted with a mixture of methylene chloride and ethyl acetate (70:30)

Sources & evidence

ORD record
ord-1b9c85b84686446ebd09e15de85684e0
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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