Réaction #68346

Équation de réaction

3,4-difluorobenzylamine

1-benzyl-6-(ethoxylcarbonyl)-2-isopropyl-1H-indole-3-carboxylic acid

Compound 39

1-benzyl-6-(ethoxylcarbonyl)-2-isopropyl-1H-indole-3-carboxylic acid

EDC

→

title compound

Ethyl 1-Benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylate

Solvants

EtOAc

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Lavagewashed with H2O, brine
2. 2
   Séchagedried over Na2SO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   AutreThe residue was purified by chromatography on silica gel (0→35% EtOAc-hexanes)

Mode opératoire

General Procedure E. To a solution of 1-benzyl-6-(ethoxylcarbonyl)-2-isopropyl-1H-indole-3-carboxylic acid (Compound 39, 1.00 g, 2.74 mmol) in CH2Cl2 (10 ml) was added EDC (1.04 g, 5.84 mmol) and DMAP (500 mg, 4.11 mmol), followed by 3,4-difluorobenzylamine (589 mg, 4.11 mmol). The reaction was stirred at room temperature for 12 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→35% EtOAc-hexanes) to yield the title compound as a yellow solid.

Source