1-Bromo-2-Chloroethane → 3-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-5,6,5'-trimethyl-[2,2']bipyridine

HRID 229091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 229091
[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][Cl:39]>CN(C)C=O>[Cl:39][CH2:38][CH2:37][O:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([O:14][C:15]3[C:16]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][N:24]=4)=[N:17][C:18]([CH3:22])=[C:19]([CH3:21])[CH:20]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 1361316196-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-ol2×

Produkt 1

HCID 577563443-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-5,6,5'-trimethyl-[2,2']bipyridineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Methoxy-4-(5,6,5′-trimethyl-[2,2′]bipyridin-3-yloxy)-quinolin-7-ol (compound 453) (30 mg) was suspended in N,N-dimethylformamide (2 ml). Potassium carbonate (107 mg) and 1-bromo-2-chloroethane (0.03 ml) were added to the suspension, and the mixture was stirred at room temperature 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-methanol to give the title compound (36 mg, yield 100%).

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-b735730beef84abca628797bd38c0e5e
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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