Reacción #5553

Ecuación de reacción

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

triethylamine

methanesulfonyl chloride

→

desired product

Rendimiento 50.8%

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

Rendimiento 50.8%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGthe mixture was stirred under ice-
3. 3
   Temperaturacooling for 1 hour
4. 4
   LavadoThe reaction mixture was washed in turn with an aqueous saturated sodium bicarbonate solution and saturated saline
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONAfter the solvent was distilled off
7. 7
   Otrothe residue was purified by column chromatography (eluent: ethyl acetate)

Procedimiento

To a solution of 5-[4-(amino)butylthio]imidazo[1,2-a]pyridine (440 mg, 1.99 mmoles) and triethylamine (0.42 ml, 3.01 mmoles) in methylene chloride (20 ml) was added methanesulfonyl chloride (0.19 ml, 2.45 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. The reaction mixture was washed in turn with an aqueous saturated sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 302 mg of the desired product (50.8%, light red brown solid).

Fuente