Reacción #5526

Ecuación de reacción

Tert-butyl dicarbonate

5-chloroimidazo[1,2-a]pyridine

4-aminobutanol

sodium hydride

→

desired product

Rendimiento 41.0%

5-[4-(amino)butoxy]imidazo[1,2-a]pyridine

Rendimiento 41.0%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at the same temperature for 5 hours
2. 2
   workup.STIRRINGwas stirred at room temperature for 13 hours
3. 3
   workup.DISTILLATIONAfter the solvent was distilled off
4. 4
   workup.ADDITIONwater was added to the residue, which
5. 5
   Extracciónwas extracted with ether twice
6. 6
   Lavadowashed with water
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off
9. 9
   workup.DISSOLUTIONThe residue was dissolved in methanol (20 ml)
10. 10
    workup.ADDITIONfollowed by the addition of conc. hydrochloric acid (20 ml)
11. 11
    workup.STIRRINGstirring at room temperature for 1 hour
12. 12
    workup.DISTILLATIONAfter the solvent was distilled off
13. 13
    workup.ADDITIONchloroform was added to the residue, which
14. 14
    Lavadowas washed with 3N NaOH
15. 15
    SecadoAfter drying over anhydrous potassium carbonate
16. 16
    workup.DISTILLATIONthe solvent was distilled off
17. 17
    OtroThe residue was purified by column chromatography (eluent: methanol/chloroform=1:5)

Procedimiento

To a suspension of 60% sodium hydride (oily; 1.32 g, 33 mmloes) in DMF (60 ml) was added a solution of 5-chloroimidazo[1,2-a]pyridine (4.59 g, 30.1 mmoles) and 4-aminobutanol (2.68 g, 30.1 mmoles) in DMF (60 ml) at room temperature with stirring and the mixture was stirred at the same temperature for 5 hours. Tert-butyl dicarbonate (9.83 g, 45 mmoles) was added to the reaction solution, which was stirred at room temperature for 13 hours. After the solvent was distilled off, water was added to the residue, which was extracted with ether twice, washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was dissolved in methanol (20 ml), followed by the addition of conc. hydrochloric acid (20 ml) and stirring at room temperature for 1 hour. After the solvent was distilled off, chloroform was added to the residue, which was washed with 3N NaOH. After drying over anhydrous potassium carbonate, the solvent was distilled off. The residue was purified by column chromatography (eluent: methanol/chloroform=1:5) to obtain 2.53 g of the desired product (40.9%, light brown oily product).

Fuente