Reacción #5544

Ecuación de reacción

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

triethylamine

methyl chloroformate

→

desired product

Rendimiento 66.9%

5-[2-(methoxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine

Rendimiento 66.9%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 20 minutes
3. 3
   LavadoThe reaction mixture was washed in turn with an aqueous sodium bicarborate solution and water
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off
6. 6
   OtroThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10)

Procedimiento

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.93 g, 10 mmoles) and triethylamine (1.53 ml, 11 mmoles) in methylene chloride (30 ml) was added methyl chloroformate (0.77 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was washed in turn with an aqueous sodium bicarborate solution and water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10) to obtain 1.68 g of the desired product (66.9%, colorless crystals).

Fuente