Reaktion #589421

Reaktionsgleichung

cyclopropyl methyl carbinol

2-(4-aminophenyl)-1-cyclobutyl-6-hydroxy-1H-indole-3-carbonitrile

4-nitrophenyl chloroformate

→

[4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester

Ausbeute 80.0%

Lösungsmittel

HCl

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 8 h at 80° C
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   EinengenThe organic layer is concentrated
4. 4
   workup.DISSOLUTIONthe residue is dissolved in EtOAc
5. 5
   Sonstigetriturated with hexane
6. 6
   FiltrationThe precipitate is collected by filtration
7. 7
   Waschenwashed with hexane
8. 8
   Sonstigedried in vacuo

Vorschrift

To a solution 2-(4-aminophenyl)-1-cyclobutyl-6-hydroxy-1H-indole-3-carbonitrile (909 mg, 3 mmol) in pyridine (5 mL) is added 4-nitrophenyl chloroformate (6 mmol) at room temperature and then stirred for 2 h at room temperature. To the reaction is added cyclopropyl methyl carbinol and then stirred for 8 h at 80° C. The reaction mixture is diluted with 1N HCl and then extracted with ethyl acetate. The organic layer is concentrated and the residue is dissolved in EtOAc and triturated with hexane. The precipitate is collected by filtration and washed with hexane and dried in vacuo to afford [4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester (996 mg, 80%).

Quelle