Reacción #5555

Ecuación de reacción

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

triethylamine

isopropyl chloroformate

→

desired product

Rendimiento 41.9%

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

Rendimiento 41.9%

Disolventes

metylene 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 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 (370 mg, 1.67 mmoles) and triethylamine (0.35 ml, 2.51 mmoles) in metylene chloride (20 ml) was added isopropyl chloroformate (0.25 g, 2.04 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 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 215 mg of the desired product (41.8%, light tan oily product).

Fuente