1-Bromo-2-Chloroethane → 3-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-5,6,6'-trimethyl-[2,2']bipyridine

HRID 229090Notes

Reaction equation

HRID 229090 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=2)=[N:17][C:18]([CH3:22])=[C:19]([CH3:21])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][CH2:38][Cl:39]>CN(C)C=O>[Cl:39][CH2:38][CH2:37][O:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([O:14][C:15]3[C:16]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=4)=[N:17][C:18]([CH3:22])=[C:19]([CH3:21])[CH:20]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 1361316246-Methoxy-4-(5,6,6'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-ol2×

Product 1

HCID 577563753-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-5,6,6'-trimethyl-[2,2']bipyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methoxy-4-(5,6,6′-trimethyl-[2,2′]bipyridin-3-yloxy)-quinolin-7-ol (compound 443) (30 mg) was dissolved in N,N-dimethylformamide (2 ml) to prepare a solution. Potassium carbonate (107 mg) and 1-bromo-2-chloroethane (0.03 ml) were added to the solution, and the mixture was stirred at room temperature 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 (37 mg, yield 100%).

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-923c0354dbb24509adc1270ec49cb3a4
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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