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

HRID 1386064Notes

Reaction equation

HRID 1386064 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:13][C:14]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([CH3:23])[C:15]=1[CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>C(#N)C.C(Cl)Cl>[CH3:11][C:9]1[N:10]=[C:3]2[C:2]([NH:1][CH2:16][C:15]3[C:14]([CH3:13])=[CH:21][C:20]([F:22])=[CH:19][C:18]=3[CH3:23])=[CH:7][CH:6]=[CH:5][N:4]2[C:8]=1[CH3:12]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amineHCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

Product 1

HCID 217173582,3-Dimethyl-8-(2,6-dimethyl-4-fluorobenzylamino)imidazo[1,2-a]pyridineYield 43.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

8-Amino-2,3-dimethylimidazo[1,2-a]pyridine (0.5 g, 3.1 mmol) was dissolved in acetonitrile (6 ml). To the solution were added 2,6-dimethyl-4-fluoro-benzylbromide (0.67 g, 3.1 mmol) and potassium carbonate (0.47 g, 3.4 mmol). The mixture was refluxed for 16 h. Methylene chloride (12 ml) and a sodium chloride solution (20 ml) was added. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The crude product was purified by chromatography (ethyl acetate:petroleum-ether 1:1). 400 mg of the title compound was obtained as a solid.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by chromatography (ethyl acetate:petroleum-ether 1:1)

Sources & evidence

ORD record
ord-b8652a32a1454d97b9542d938a895733
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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