Reacción #5548

Ecuación de reacción

5-mercaptoimidazo[1,2-a]pyridine

N-[4-(bromo)butyl]phthalimide

triethylamine

→

desired product

Rendimiento 64.1%

5-[4-(phthalimido)butylthio]imidazo[1,2-a]pyridine

Rendimiento 64.1%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaat reflux for 45 minutes
3. 3
   workup.DISTILLATIONAfter the solvent was distilled off
4. 4
   workup.ADDITIONchloroform was added to the residue, which
5. 5
   Lavadowas washed with saturated saline
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off
8. 8
   OtroThen, the residue was purified by column chromatography (eluent: ethyl acetate)

Procedimiento

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00g, 20 mmoles) and N-[4-(bromo)butyl]phthalimide (6.21 g, 22 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 1 hour and heated at reflux for 45 minutes. After the solvent was distilled off, chloroform was added to the residue, which was washed with saturated saline, dried over anhydrous magnesium sulfate and the solvent was distilled off. Then, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 4.50 g of the desired product (64.1%, pale yellow crystals).

Fuente