Reacción #68326

Ecuación de reacción

1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide

Compound 8

1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide

dimethylcarbamyl chloride

→

title compound

Rendimiento 82.0%

1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indol-6-yl Dimethylcarbamate

Rendimiento 82.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with water
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe combined organic layer was washed with water, brine
4. 4
   Secadodried over Na2SO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Procedimiento

General Procedure B. To a solution of 1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide (Compound 8, 18mg, 0.041mol) in pyridine (1 ml) was added dimethylcarbamyl chloride (40 μl, 0.41 mmol) and stirred at room temperature overnight. The reaction was quenched with water, extracted with ethyl acetate. The combined organic layer was washed with water, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a white solid (17 mg, 82%).

Fuente