Potassium Iodide → HCID 21717342, compound

HRID 1386076Notes

Reaction equation

HRID 1386076 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:14]([C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([CH3:25])[C:17]=1[CH2:18]Br)[CH3:15].[I-].[K+].C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC>[CH2:14]([C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([CH3:25])[C:17]=1[CH2:18][NH:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH3:15]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 21717327HCID 21717327, compoundHCID 22672632HCID 22672632, compound

Product 1

HCID 21717342HCID 21717342, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

8-Amino-2,3,6-trimethylimidazo[1,2-a]pyridine (0.38 g, 2.16 mmol) and 2-ethyl-4-fluoro-6-methylbenzylbromide (0.50 g, 2.16 mmol) were dissolved in 10 ml dimethoxyethane. Potassium iodide (0.2 g, 1.2 mmol) and Na2CO3 (0.4 g, 3.8 mmol) were added and the mixture was refluxed for 6 hours. The solvent was evaporated and the residue was purified by column chromatography on silica gel using a mixture of methylene chloride and ethyl acetate (60:40) as eluent. 203 mg (29%) of the title compound was obtained.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography on silica gel using
  4. additiona mixture of methylene chloride and ethyl acetate (60:40) as eluent

Sources & evidence

ORD record
ord-14bc3e2bfc4f43fc9ca11e04c3ae6f34
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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