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2-Iodo-6-methylpyridin-3-ol → 7-Benzyloxy-4-(2-iodo-6-methyl-pyridin-3-yloxy)-6-methoxyquinoline

HRID 228926
Notes
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Reaction equation

HRID 228926 reaction equation
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[CH:13][CH:12]=1>CN(C1C=CN=CC=1)C.ClC1C=CC=CC=1Cl>[CH2:24]([O:23][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([O:8][C:7]3[C:2]([I:1])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=3)=[CH:12][CH:13]=[N:14]2)=[CH:19][C:18]=1[O:21][CH3:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 899572-Iodo-6-methylpyridin-3-olHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Product 1

HCID 230783237-Benzyloxy-4-(2-iodo-6-methyl-pyridin-3-yloxy)-6-methoxyquinolineYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 72391,2-Dichlorobenzene
Solvent

Conditions

Temperature
125 °C

Procedure

2-Iodo-6-picolin-3-ol (10 g), 4-chloro-7-benzyloxy-6-methoxyquinoline (6.8 g), and 4-(N,N-dimethylamino)-pyridine (12.2 g) were dissolved in 1,2-dichlorobenzene (400 ml) to prepare a solution, and the mixture was stirred at 125° C. overnight. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was added to the residue, the mixture was extracted with chloroform, and the chloroform layer was then 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 column chromatography using chloroform-acetone to give 7-benzyloxy-4-(2-iodo-6-methyl-pyridin-3-yloxy)-6-methoxy-quinoline (5.2 g, yield 31%).

Workup

  1. customto prepare a solution
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washthe chloroform layer was then washed with water
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7827b17d3f3644edb1816e665f69888b
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