Water → 3-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,5'-trimethyl-[2,2']bipyridine

HRID 229077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 229077
[CH3:1][C:2]1[CH:3]=[C:4]([OH:16])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=2)=[N:6][C:7]=1[CH3:8].[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](Cl)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C1C=CN=CC=1.CS(C)=O>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([O:16][C:4]3[C:5]([C:9]4[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=4)=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinolineHCID 1363851085,6,5'-Trimethyl-[2,2']bipyridin-3-ol

Produkt 1

HCID 577563763-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,5'-trimethyl-[2,2']bipyridineAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

5,6,5′-Trimethyl-[2,2′]bipyridin-3-ol (300 mg), 7-benzyloxy-4-chloro-6-methoxyquinoline (1.26 g), 4-dimethylaminopyridine (513 mg), and cesium carbonate (1.37 g) were suspended in dimethyl sulfoxide (6 ml), and the suspension was stirred at 130° C. overnight. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with chloroform. The chloroform 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 column chromatography using chloroform-methanol to give the title compound (504 mg, yield 75%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was then washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7a74ccbc416240aca5b4261b7eb0aab9
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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