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Water → 4-(4,5-Dimethyl-2-pyridin-3-yl-phenoxy)-6,7-dimethoxy-quinoline

HRID 228694
Notes
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Reaction equation

HRID 228694 reaction equation
I[C:2]1[CH:22]=[C:21]([CH3:23])[C:20]([CH3:24])=[CH:19][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:23][C:21]1[C:20]([CH3:24])=[CH:19][C:3]([O:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=3)[N:8]=[CH:7][CH:6]=2)=[C:2]([C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)[CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 230783614-(2-Iodo-4,5-dimethyl-phenoxy)-6,7-dimethoxyquinoline2×

Product 1

HCID 230782734-(4,5-Dimethyl-2-pyridin-3-yl-phenoxy)-6,7-dimethoxy-quinolineYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-(2-Iodo-4,5-dimethyl-phenoxy)-6,7-dimethoxyquinoline (compound 164) (59 mg), pyridine-3-boronic acid (33 mg), and tetrakistriphenylphosphine palladium (10 mg) were dissolved in N,N-dimethylformamide (4 ml), a 2 M aqueous potassium carbonate solution (0.5 ml) was added to the reaction system, and the mixture was stirred at 100° C. for 30 min. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (13 mg, yield 25%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was then washed with water
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThe solvent was removed
  5. distillationby distillation under the reduced pressure
  6. customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-015b3acdc79b4be191c997307d8b5d49
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