Water → [3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanol

HRID 228752

Reaktionsgleichung

Reaktionsgleichung von HRID 228752
I[C:2]1[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[C:4]([CH3:23])[N:3]=1.CCCCCC.C([Li])CCC.[CH3:35][C:36]1[N:41]=[C:40]([CH:42]=[O:43])[CH:39]=[CH:38][CH:37]=1.O>O1CCCC1>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:21][CH3:22])[N:12]=[CH:11][CH:10]=[C:9]2[O:8][C:7]1[C:2]([CH:42]([C:40]2[CH:39]=[CH:38][CH:37]=[C:36]([CH3:35])[N:41]=2)[OH:43])=[N:3][C:4]([CH3:23])=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 100936734-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline2×HCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 23078288[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanolAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

4-(2-Iodo-6-methyl-pyridin-3-yloxy)-6,7-dimethoxyquinoline (compound 116) (100 mg) was dissolved in tetrahydrofuran (7 ml) to prepare a solution which was then brought to −78° C. n-Butyllithium hexane solution (0.22 ml) was slowly added dropwise thereto, and the mixture was stirred at −78° C. for 20 min. 6-Methyl-2-pyridine-carbaldehyde (57 mg) was dissolved in tetrahydrofuran (7 ml) to prepare a solution which was then added dropwise to the reaction solution, followed by stirring at room temperature for 5 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give [3-(6,7-dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanol (73 mg, yield 73%).

Aufarbeitung

  1. customto prepare a solution which
  2. customwas then brought to −78° C.
  3. additionwas slowly added dropwise
  4. customto prepare a solution which
  5. additionwas then added dropwise to the reaction solution
  6. stirringby stirring at room temperature for 5 hr
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe ethyl acetate layer was then washed with saturated brine
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. customThe solvent was removed by distillation under the reduced pressure
  11. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0d51150efd0946e6bcbbdc7952f139f4
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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