Water → {2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}(5-isoxazolyl)methanone

HRID 228582

Reaktionsgleichung

Reaktionsgleichung von HRID 228582
Br[C:2]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.C([Li])CCC.CCCCCC.[O:35]1[C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=[N:36]1.O>O1CCCC1>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:17][CH3:18])[N:8]=[CH:7][CH:6]=[C:5]2[O:4][C:3]1[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:2]=1[C:40]([C:39]1[O:35][N:36]=[CH:37][CH:38]=1)=[O:41]

Komponenten

6

Edukt 4

HCID 962WaterHCID 2736707Isoxazole-5-carbonyl chlorideHCID 230783624-(2-Bromo-4-methylphenoxy)-6,7-dimethoxyquinolineHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 24879100{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}(5-isoxazolyl)methanoneAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

4-(2-Bromo-4-methylphenoxy)-6,7-dimethoxyquinoline (100 mg) was dissolved in tetrahydrofuran (6 ml) to prepare a solution which was then cooled to −78° C. A 1.59 M n-butyllithium/hexane solution (0.4 ml) was added to the solution, and the mixture was stirred at −78° C. for 20 min. Isoxazole-5-carbonyl chloride (0.2 ml) was added to the reaction solution, and the mixture was stirred at room temperature overnight. Further, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (27 mg, yield 26%).

Aufarbeitung

  1. customto prepare a solution which
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was then washed with water and saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. distillationby distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-25a0a83dff7e4caa846058ecd1d22579
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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