Sodium Iodide → 3-Carboethoxy-2,6-dimethyl-8-(2-ethyl-4-fluoro-6-methylbenzylamino)imidazo[1,2-a]pyridine

HRID 1386098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386098
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:18]([C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([CH3:29])[C:21]=1[CH2:22]Br)[CH3:19].[C:30](=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH:16]([O:15][CH:27]([CH3:26])[CH3:20])([CH3:17])[CH3:30].[C:13]([C:9]1[N:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([NH:1][CH2:22][C:21]3[C:24]([CH3:29])=[CH:25][C:26]([F:28])=[CH:27][C:20]=3[CH2:18][CH3:19])[C:3]2=[N:11][C:10]=1[CH3:12])([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 21717327HCID 21717327, VerbindungHCID 226725728-Amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridine

Produkt 2

HCID 7914Diisopropyl EtherHCID 217173533-Carboethoxy-2,6-dimethyl-8-(2-ethyl-4-fluoro-6-methylbenzylamino)imidazo[1,2-a]pyridineAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred mixture of (0.7 g, 3.0 mmol) 8-amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridine, (0.8 g, 3.5 mmol) 2-ethyl-4-fluoro-6-methylbenzylbromide, (0.7 g, 4.8 mmol) potassium carbonate and (0.1 g) sodium iodide in 15 ml acetonitrile was refluxed over night. After evaporation of the solvent under reduced pressure the residue was dissolved in dichloromethane and washed with water, the organic layer was separated dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluent petroleum ether (40-60):isopropyl ether 7:3 to give 0.4 g, (35%) of the title compound.

Aufarbeitung

  1. temperaturewas refluxed over night
  2. customAfter evaporation of the solvent under reduced pressure the residue
  3. dissolutionwas dissolved in dichloromethane
  4. washwashed with water
  5. customthe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel, eluent petroleum ether (40-60)

Quellen und Nachweise

ORD-Eintrag
ord-c2939ce61ffc4a2dad02096fcc0430c1
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265415B1

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