Potassium Iodide → Ethyl 8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine-2-carboxylate

HRID 1369586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1369586
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:19]=1[CH2:20]Cl.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(#N)C>[CH3:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:19]=1[CH2:20][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 22672637Ethyl 8-amino-3-methylimidazo[1,2-a]pyridine-2-carboxylate

Produkt 1

HCID 22672581Ethyl 8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine-2-carboxylateAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Ethyl 8-amino-3-methylimidazo[1,2-a]pyridine-2-carboxylate (4.6 g, 21 mmol), 2,6-dimethylbenzyl chloride (3.2 g, 21 mmol), sodium carbonate (4.4 g, 42 mmol) and a cat. amount of potassium iodide were added to acetonitrile (50 ml) and refluxed for 3 h. stirred for 20 h. at room temperature and refluxed for 1 h. The solids were removed by filtration and the solvents were evaporated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride:methanol (10:1) as eluent and crystallization from ethyl acetate gave 4.0 g (56%) of the desired product.

Aufarbeitung

  1. temperaturerefluxed for 3 h.
  2. temperaturerefluxed for 1 h
  3. customThe solids were removed by filtration
  4. customthe solvents were evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with water
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. customevaporated under reduced pressure
  10. customPurification of the residue by column chromatography on silica gel
  11. customcrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2a6b0edca7704525a1b552c0ed117fb7
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06579884B1

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