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2-Bromoethanol → 2-[4-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-6-methoxy-quinolin-7-yloxy]-ethanol

HRID 228939
Notes
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Reaction equation

HRID 228939 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([OH:28])=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][CH:17]=2)[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][CH2:37][OH:38]>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([O:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:28][CH2:36][CH2:37][OH:38])=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][CH:17]=2)[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:6][C:7]=1[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 1361316214-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-6-methoxy-quinolin-7-ol2×

Product 1

HCID 577563682-[4-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-6-methoxy-quinolin-7-yloxy]-ethanolYield 88%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
70 °C

Procedure

4-(5,6-Dimethyl-[2,2′]bipyridin-3-yloxy)-6-methoxy-quinolin-7-ol (compound 338) (80 mg) was dissolved in N,N-dimethylformamide (2 ml) to prepare a solution. Potassium carbonate (89 mg) and 2-bromoethanol (0.05 ml) were added to the solution, and the mixture was stirred at 70° C. overnight. The solvent was removed by distillation under the reduced pressure, water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and was dried over anhydrous sodium sulfate, the solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (77 mg, yield 88%).

Workup

  1. customto prepare a solution
  2. customThe solvent was removed by distillation under the reduced pressure, water
  3. additionwas then added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with saturated brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customthe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-ac33cefb49f64c04a49d6b65252f460b
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