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

HRID 1386077Notes

Reaction equation

HRID 1386077 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]2[C:11]=1[CH3:12].[CH3:13][C:14]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([CH3:23])[C:15]=1[CH2:16]Br.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CC(C)=O>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:16][C:15]3[C:14]([CH3:13])=[CH:21][C:20]([F:22])=[CH:19][C:18]=3[CH3:23])=[CH:8][CH:7]=[CH:6][N:5]2[C:11]=1[CH3:12]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 224679492,3-Dimethylimidazo[1,2-a]pyridin-8-olHCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

Product 1

HCID 217173212,3-Dimethyl-8-(2,6-dimethyl-4-fluorobenzyloxy)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

2,3-Dimethyl-8-hydroxyimidazo[1,2-a]pyridine (1.7 g, 10 mmol), 2,6-dimethyl-4-fluorobenzylbromide (2.3 g, 10 mmol), sodium iodide (0.5 g, 0.3 mmol) and sodium carbonate (2.6 g, 28 mmol) were added to acetone (75 ml) and the mixture was refluxed for 6 h. Methylene chloride was added and the mixture was filtered and the solvents were evaporated under reduced pressure. Purification by column chromatography on silica gel using methylene chloride:ethylacetate(1:2) as eluent gave the title compound as a white powder. (0.85 g, 28%)

Workup

  1. temperaturethe mixture was refluxed for 6 h
  2. filtrationthe mixture was filtered
  3. customthe solvents were evaporated under reduced pressure
  4. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-3b8a25f89b7141168becd8f094f7a95f
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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