Sodium Iodide → 3-Carboethoxy-2,6-dimethyl-8-(2-ethyl-4-fluoro-6-methylbenzylamino)imidazo[1,2-a]pyridine

HRID 1386098Notes

Reaction equation

HRID 1386098 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:18]([C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([CH3:29])[C:21]=1[CH2:22]Br)[CH3:19].[C:30](=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH:16]([O:15][CH:27]([CH3:26])[CH3:20])([CH3:17])[CH3:30].[C:13]([C:9]1[N:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([NH:1][CH2:22][C:21]3[C:24]([CH3:29])=[CH:25][C:26]([F:28])=[CH:27][C:20]=3[CH2:18][CH3:19])[C:3]2=[N:11][C:10]=1[CH3:12])([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 21717327HCID 21717327, compoundHCID 226725728-Amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridine

Product 2

HCID 7914Diisopropyl EtherHCID 217173533-Carboethoxy-2,6-dimethyl-8-(2-ethyl-4-fluoro-6-methylbenzylamino)imidazo[1,2-a]pyridineYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of (0.7 g, 3.0 mmol) 8-amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridine, (0.8 g, 3.5 mmol) 2-ethyl-4-fluoro-6-methylbenzylbromide, (0.7 g, 4.8 mmol) potassium carbonate and (0.1 g) sodium iodide in 15 ml acetonitrile was refluxed over night. After evaporation of the solvent under reduced pressure the residue was dissolved in dichloromethane and washed with water, the organic layer was separated dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluent petroleum ether (40-60):isopropyl ether 7:3 to give 0.4 g, (35%) of the title compound.

Workup

  1. temperaturewas refluxed over night
  2. customAfter evaporation of the solvent under reduced pressure the residue
  3. dissolutionwas dissolved in dichloromethane
  4. washwashed with water
  5. customthe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel, eluent petroleum ether (40-60)

Sources & evidence

ORD record
ord-c2939ce61ffc4a2dad02096fcc0430c1
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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