Reaction #316189

Reaction equation

3-[7-Hydroxy-6-methoxy-quinolin-4-yloxy]-2-methyl-[1,8]naphthyridine

Potassium carbonate

4-bromo-1-butanol

→

title compound

Yield 35.0%

4-[6-Methoxy-4-(2-methyl-[1,8]naphthyridin-3-yloxy)-quinolin-7-yloxy]-butan-1-ol

Yield 35.0%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Otherto prepare a solution
2. 2
   OtherThe solvent was removed by distillation under the reduced pressure
3. 3
   workup.ADDITIONWater was then added to the residue
4. 4
   Extractionthe mixture was extracted with chloroform
5. 5
   WashThe chloroform layer was washed with saturated brine
6. 6
   Dryingwas dried over anhydrous sodium sulfate
7. 7
   OtherThe solvent was removed by distillation under the reduced pressure
8. 8
   Otherthe residue was purified by thin layer chromatography

Procedure

3-[7-Hydroxy-6-methoxy-quinolin-4-yloxy]-2-methyl-[1,8]naphthyridine (45 mg) was dissolved in N,N-dimethylformamide (2 ml) to prepare a solution. Potassium carbonate (56 mg) and 4-bromo-1-butanol (62 mg) 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-acetone to give the title compound (19 mg, yield 35%).

Source