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Water → 4-[2-(2,4-Difluoro-phenyl)-quinolin-3-yloxy]-6,7-dimethoxy-quinoline

HRID 228850
Notes
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Reaction equation

HRID 228850 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]([OH:19])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][CH:22]=1.O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]([O:19][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][CH:22]=2)=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 230785092-(2,4-Difluoro-phenyl)-quinolin-3-ol

Product 1

HCID 577563324-[2-(2,4-Difluoro-phenyl)-quinolin-3-yloxy]-6,7-dimethoxy-quinolineYield 27.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 7239
1,2-Dichlorobenzene
Solvent

Conditions

Temperature
145 °C

Procedure

2-(2,4-Difluoro-phenyl)-quinolin-3-ol (220 mg), 4-chloro-6,7-dimethoxyquinoline (237 mg), and 4-dimethylaminopyridine (380 mg) were suspended in o-dichlorobenzene (10 ml), and the suspension was stirred at 145° C. for 8 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (104 mg, yield 27%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-d6267098dd834318b589a62b702536c1
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes