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2-Bromoethanol → 2-[6-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-yloxy]-ethanol

HRID 229084
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 229084
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][N:24]=2)=[N:17][C:18]([CH3:22])=[C:19]([CH3:21])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][CH2:38][OH:39]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:37][CH2:38][OH:39])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][N:24]=2)=[N:17][C:18]([CH3:22])=[C:19]([CH3:21])[CH:20]=1
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Komponenten

5

Edukt 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 1361316196-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-ol2×

Produkt 1

HCID 577563942-[6-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-yloxy]-ethanolAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

6-Methoxy-4-(5,6,5′-trimethyl-[2,2′]bipyridin-3-yloxy)-quinolin-7-ol (compound 453) (50 mg) was suspended in N,N-dimethylformamide (2 ml). Potassium carbonate (54 mg) and 2-bromoethanol (0.03 ml) were added to the suspension, and the mixture was stirred at 70° C. overnight. The solvent was removed by distillation under the reduced pressure, water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was 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 the title compound (34 mg, yield 61%).

Aufarbeitung

  1. customThe solvent was removed by distillation under the reduced pressure, water
  2. additionwas then added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. washThe chloroform layer was washed with saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b6801f99cd2a438cb641cca5dec0e806
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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