Sodium Iodide → 3-Carboethoxy-8-(2,6-dimethyl-4-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 1386091Notes

Reaction equation

HRID 1386091 reaction equation
[C:1]([C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([OH:15])[C:9]2=[N:8][C:7]=1[CH3:16])([O:3][CH2:4][CH3:5])=[O:2].[CH3:17][C:18]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([CH3:27])[C:19]=1[CH2:20]Br.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH2:20][C:19]3[C:18]([CH3:17])=[CH:25][C:24]([F:26])=[CH:23][C:22]=3[CH3:27])[C:9]2=[N:8][C:7]=1[CH3:16])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 21717316Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylateHCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

Product 1

HCID 217173463-Carboethoxy-8-(2,6-dimethyl-4-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridineYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-carboethoxy-8-hydroxy-2-methylimidazo[1,2-a]pyridine (1.5 g, 6.8 mmol), 2,6-dimethyl-4-fluorobenzylbromide (1.6 g, 7.5 mmol), sodium iodide (0.1 g), potassium carbonate (1.9 g, 13.6 mmol) and acetonitrile (50 ml) was refluxed for over night. The solvent was removed in vacuo. The residue was dissolved in CH2Cl2, washed with water, dried over Na2SO4 and evaporated. The residue was chromatographed on silica, eluting with heptane:isopropyl ether(1:2) to give 2.0 g (83%) of the desired product.

Workup

  1. temperaturewas refluxed for over night
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was chromatographed on silica
  8. washeluting with heptane:isopropyl ether(1:2)

Sources & evidence

ORD record
ord-7f5adcc52cc344599489a4a9a2a1bda9
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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