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

HRID 1386091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386091
[C:1]([C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([OH:15])[C:9]2=[N:8][C:7]=1[CH3:16])([O:3][CH2:4][CH3:5])=[O:2].[CH3:17][C:18]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([CH3:27])[C:19]=1[CH2:20]Br.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH2:20][C:19]3[C:18]([CH3:17])=[CH:25][C:24]([F:26])=[CH:23][C:22]=3[CH3:27])[C:9]2=[N:8][C:7]=1[CH3:16])([O:3][CH2:4][CH3:5])=[O:2]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 21717316Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylateHCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

Produkt 1

HCID 217173463-Carboethoxy-8-(2,6-dimethyl-4-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 3-carboethoxy-8-hydroxy-2-methylimidazo[1,2-a]pyridine (1.5 g, 6.8 mmol), 2,6-dimethyl-4-fluorobenzylbromide (1.6 g, 7.5 mmol), sodium iodide (0.1 g), potassium carbonate (1.9 g, 13.6 mmol) and acetonitrile (50 ml) was refluxed for over night. The solvent was removed in vacuo. The residue was dissolved in CH2Cl2, washed with water, dried over Na2SO4 and evaporated. The residue was chromatographed on silica, eluting with heptane:isopropyl ether(1:2) to give 2.0 g (83%) of the desired product.

Aufarbeitung

  1. temperaturewas refluxed for over night
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was chromatographed on silica
  8. washeluting with heptane:isopropyl ether(1:2)

Quellen und Nachweise

ORD-Eintrag
ord-7f5adcc52cc344599489a4a9a2a1bda9
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265415B1

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