Reaction #316252

Reaction equation

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

compound 338

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

Potassium carbonate

4-bromo-1-butanol

Water

→

title compound

Yield 48.4%

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

Yield 48.4%

Solvents

N,N-dimethylformamide

Conditions

Workup

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

Procedure

4-(5,6-Dimethyl-[2,2′]bipyridin-3-yloxy)-6-methoxy-quinolin-7-ol (compound 338) (45 mg) was suspended in N,N-dimethylformamide (4 ml). Potassium carbonate (50 mg) and 4-bromo-1-butanol (55 mg) were added to the suspension, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. 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 (26 mg, yield 48%).

Source