Dimethylformamide → 7-Benzyloxy-6-methoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinoline

HRID 228927

Reaktionsgleichung

Reaktionsgleichung von HRID 228927
CN(C)C=O.[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([O:24][C:25]3[C:26](I)=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=3)=[CH:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:33][CH3:34])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([Sn](CCCC)(CCCC)[C:40]1[S:41][CH:42]=[CH:43][N:44]=1)CCC>[Cu]=O.O>[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([O:24][C:25]3[C:26]([C:40]4[S:41][CH:42]=[CH:43][N:44]=4)=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=3)=[CH:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:33][CH3:34])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 230783237-Benzyloxy-4-(2-iodo-6-methyl-pyridin-3-yloxy)-6-methoxyquinoline

Produkt 1

HCID 230782767-Benzyloxy-6-methoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinolineAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14829Copper oxideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

N,N-Dimethylformamide (2 ml) was added to 7-benzyloxy-4-(2-iodo-6-methyl-pyridin-3-yloxy)-6-methoxyquinoline (100 mg), tetrakistriphenylphosphine palladium (23 mg), tri-n-butyl-(thiazol-2-yl)-tin (113 mg), and copper(II) oxide (32 mg) under an argon atmosphere, and the mixture was stirred at 100° C. overnight. The reaction solution was cooled to room temperature, water was then added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water 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 hexane-acetone to give the title compound (43 mg, yield 46%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  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-8197771968384500918644a8315bf92d
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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