Reaktion #365286

Reaktionsgleichung

ammonia

1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxylic acid

1-hydroxybenzotriazole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxamide

Ausbeute 82.2%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was partitioned between ethyl acetate and water
2. 2
   Waschenthe organic phase was washed with 1N hydrochloric acid and brine
3. 3
   Trocknendried over sodium sulfate
4. 4
   Sonstigeevaporated in vacuo
5. 5
   workup.ADDITIONThe crystalline residue was recyrystallized from a mixture of ethyl acetate and hexane

Vorschrift

To a solution of 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxylic acid (150 mg) in dimethylformamide (3 ml) were added 1-hydroxybenzotriazole (102 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (109 mg). After stirred at 20° C. over night, the resulting mixture was poured into 28% aqueous ammonia (5 ml). The mixture was partitioned between ethyl acetate and water, and the organic phase was washed with 1N hydrochloric acid and brine, dried over sodium sulfate and evaporated in vacuo. The crystalline residue was recyrystallized from a mixture of ethyl acetate and hexane to give 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxamide (123 mg) as colorless crystals.

Quelle