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Morpholine → [4-(6,7-Dimethoxyquinolin-4-yloxy)phenyl]-(4-morpholin-4-ylphenyl)amine

HRID 1727864
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1727864
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[C:48]1[CH:53]=[CH:52][C:51]([NH:54][C:55]2[CH:60]=[CH:59][C:58]([O:61][C:62]3[C:71]4[C:66](=[CH:67][C:68]([O:74][CH3:75])=[C:69]([O:72][CH3:73])[CH:70]=4)[N:65]=[CH:64][CH:63]=3)=[CH:57][CH:56]=2)=[CH:50][CH:49]=1.[NH:76]1[CH2:81][CH2:80][O:79][CH2:78][CH2:77]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:73][O:72][C:69]1[CH:70]=[C:71]2[C:66](=[CH:67][C:68]=1[O:74][CH3:75])[N:65]=[CH:64][CH:63]=[C:62]2[O:61][C:58]1[CH:59]=[CH:60][C:55]([NH:54][C:51]2[CH:52]=[CH:53][C:48]([N:76]3[CH2:81][CH2:80][O:79][CH2:78][CH2:77]3)=[CH:49][CH:50]=2)=[CH:56][CH:57]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 23022618(4-Bromophenyl)-[4-(6,7-dimethoxy-4-quinolyloxy)phenyl]amine

Produkt 1

HCID 23022692[4-(6,7-Dimethoxyquinolin-4-yloxy)phenyl]-(4-morpholin-4-ylphenyl)amineAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Palladium acetate (18 mg) and (+)-BINAP (70 mg) were dissolved in toluene (1.5 ml), and the solution was stirred at room temperature for 5 min. (4-Bromophenyl)-[4-(6,7-dimethoxy-4-quinolyloxy)phenyl]amine (100 mg), morpholine (0.15 ml), and cesium carbonate (200 mg) were added in that order to the reaction solution, and the mixture was stirred at 80° C. overnight. The insolubles were removed by filtration, and the solvent was then removed by evaporation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel using chloroform/acetone to give the title compound (10 mg, yield 9%).

Aufarbeitung

  1. additionwere added in that order to the reaction solution
  2. customThe insolubles were removed by filtration
  3. customthe solvent was then removed by evaporation under the reduced pressure
  4. customThe residue was purified by thin-layer chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-32ad09508d2e4fd7820c18314e8721a4
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07495104B2

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