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

HRID 1727864
Notes
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Reaction equation

HRID 1727864 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-32ad09508d2e4fd7820c18314e8721a4
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495104B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes