Sodium Iodide → 6-bromo-N-[(2,6-dimethylphenyl)methyl]-2,3-dimethylimidazo[1,2-a]pyridin-8-amine

HRID 1386061Notes

Reaction equation

HRID 1386061 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]([Br:8])[CH:7]=1.[CH3:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:16]=1[CH2:17]Cl.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].CC1C(C)=CC=CC=1CCl>CC(C)=O>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][CH2:17][C:16]2[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:15]=2[CH3:14])[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 3470371-(Chloromethyl)-2,3-dimethylbenzeneHCID 217173556-Bromo-2,3-dimethylimidazo[1,2-a]pyridin-8-ylamine

Product 1

HCID 217173516-bromo-N-[(2,6-dimethylphenyl)methyl]-2,3-dimethylimidazo[1,2-a]pyridin-8-amineYield 80.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 8-amino-6-bromo-2,3-dimethylimidazo[1,2-a]pyridine (1.2 g, 5.0 mmol), 2,6-dimethylbenzylchloride (0.772 g, 5.0 mmol), sodium carbonate (0.8 g), sodium iodide (0.2 g) and acetone (45 ml) was stirred overnight. More 2,3-dimethylbenzylchloride (0.285 g) was added and the reaction mixture was refluxed for 5 h. After addition of acetone the reaction mixture was filtered. The solvent was removed in vacuo and the residue was dissolved in CH2Cl2, washed with NaHCO3, dried over Na2SO4 and evaporated. The crude product dissolved in ethyl acetate and petroleum ether was added. Filtration and evaporation of the solvent gave a residue which was recrystallized from ethyl acetate to give 1.45 g of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. filtrationwas filtered
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in CH2Cl2
  5. washwashed with NaHCO3
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. dissolutionThe crude product dissolved in ethyl acetate
  9. additionpetroleum ether was added
  10. filtrationFiltration and evaporation of the solvent
  11. customgave a residue which
  12. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d5960556232b4a97a78e16906891498a
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

Loading…