Reacción #11970

Ecuación de reacción

compound

Methyl 4-bromomethyl-1-naphthalene Carboxylate

potassium carbonate

2-aminopyridine

→

title compound

Rendimiento 9.5%

4-(2-pyridyl)aminomethylnaphthalene-1-carboxylic acid

Rendimiento 9.5%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter the reaction
2. 2
   Otrothe solvent was removed by distillation
3. 3
   workup.DISSOLUTIONthe residue was dissolved in chloroform
4. 4
   LavadoThe organic layer was washed with 1 mol/l aqueous solution of hydrochloric acid and saturated brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   OtroThen, the solvent was removed by distillation
7. 7
   workup.DISSOLUTIONThe residue was dissolved in DMF (44 ml)
8. 8
   workup.ADDITION(1.58 ml) and di-t-butyldicarbonate (2.60 ml) were added
9. 9
   workup.STIRRINGthe mixture was stirred for 6 hours at room temperature
10. 10
    OtroAfter the reaction
11. 11
    Otrothe solvent was removed by distillation
12. 12
    workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
13. 13
    LavadoThe solution was washed with 0.5 mol/l aqueous solution of hydrochloric acid and saturated brine
14. 14
    Secadodried over anhydrous sodium sulfate
15. 15
    OtroThe solvent was removed by distillation
16. 16
    workup.DISSOLUTIONThe residue was dissolved in methanol (6 ml)
17. 17
    workup.ADDITION1 mol/l aqueous solution of sodium hydroxide (6 ml) was added
18. 18
    OtroAfter the reaction for one day
19. 19
    Concentraciónthe reaction solution was concentrated
20. 20
    workup.DISSOLUTIONThe residue was dissolved again in methanol and neutralized with ion-exchange resin CG50
21. 21
    OtroThe resin was removed by filtration
22. 22
    ConcentraciónThe filtrate was concentrated
23. 23
    OtroThe residue was purified by silica gel column chromatography (15 g, chloroform/methanol=5/1)

Procedimiento

The compound obtained in Example 17-2 (1.6728 g) was dissolved in DMF (33 ml). After the addition of potassium carbonate (1.66 g) and 2-aminopyridine (0.68 g), the mixture was stirred for 15 hours at room temperature. After the reaction, the solvent was removed by distillation and the residue was dissolved in chloroform. The organic layer was washed with 1 mol/l aqueous solution of hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. Then, the solvent was removed by distillation. The residue was dissolved in DMF (44 ml). Triethylamine. (1.58 ml) and di-t-butyldicarbonate (2.60 ml) were added and the mixture was stirred for 6 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved in ethyl acetate. The solution was washed with 0.5 mol/l aqueous solution of hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was dissolved in methanol (6 ml), and 1 mol/l aqueous solution of sodium hydroxide (6 ml) was added. After the reaction for one day, the reaction solution was concentrated. The residue was dissolved again in methanol and neutralized with ion-exchange resin CG50. The resin was removed by filtration. The filtrate was concentrated. The residue was purified by silica gel column chromatography (15 g, chloroform/methanol=5/1) to obtain the title compound (159 mg) as a colorless viscous liquid.

Fuente