Reaction #316251

Reaction equation

4-(5,6-Dimethyl-[2,3′]bipyridin-3-yloxy)-6-methoxy-quinolin-7-ol

compound 345

4-(5,6-Dimethyl-[2,3′]bipyridin-3-yloxy)-6-methoxy-quinolin-7-ol

Potassium carbonate

4-bromo-1-butanol

Water

→

title compound

Yield 35.4%

4-[4-(5,6-Dimethyl-[2,3′]bipyridin-3-yloxy)-6-methoxy-quinolin-7-yloxy]-butan-1-ol

Yield 35.4%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Otherto prepare a solution
2. 2
   Extractionthe mixture was extracted with ethyl acetate
3. 3
   Washthe ethyl acetate layer was then washed with saturated brine
4. 4
   Dryingwas dried over anhydrous sodium sulfate
5. 5
   OtherThe solvent was removed by distillation under the reduced pressure
6. 6
   Otherthe residue was purified by thin layer chromatography

Procedure

4-(5,6-Dimethyl-[2,3′]bipyridin-3-yloxy)-6-methoxy-quinolin-7-ol (compound 345) (45 mg) was dissolved in N,N-dimethylformamide (2 ml) to prepare a solution. Potassium carbonate (50 mg) and 4-bromo-1-butanol (55 mg) were added to the solution, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, the mixture was extracted with ethyl acetate, and the ethyl acetate layer was then 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-acetone to give the title compound (19 mg, yield 35%).

Source