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

HRID 1727864
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HRID 1727864 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-32ad09508d2e4fd7820c18314e8721a4
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07495104B2

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