Réaction #68392

Équation de réaction

ethyl4-(1-(3,4-difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate

Compound 114

ethyl4-(1-(3,4-difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate

→

title compound

Ethyl 2-tert-Butyl-3-(3,4-difluorobenzylcarbamoyl)-1H-indole-6-carboxylate

Solvants

MeOH

NH4Cl

Conditions de réaction

Traitement

1. 1
   Filtrationfiltered
2. 2
   Concentrationconcentrated
3. 3
   ExtractionThe remaining aqueous suspension was extracted with EtOAc (×3)
4. 4
   LavageThe combined organic layer was washed with brine
5. 5
   Séchagedried over Na2SO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutreThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Mode opératoire

General Procedure R. To a solution of ethyl4-(1-(3,4-difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate (Compound 114, 91 mg, 0.20 mmol) in MeOH (10 ml) and saturated aqueous NH4Cl (5 ml) was added zinc dust (320 mg, 4.9 mmol). The mixture was stirred at room temperature for 0.5 h, filtered and concentrated. The remaining aqueous suspension was extracted with EtOAc (×3). The combined organic layer was washed with 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.

Source