Réaction #5555

Équation de réaction

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

triethylamine

isopropyl chloroformate

→

desired product

Rendement 41.9%

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

Rendement 41.9%

Solvants

metylene chloride

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source