Reaktion #339787

Reaktionsgleichung

Rac-cyclopropyl methyl carbinol

2-(4-Aminophenyl)-1-cyclobutyl-6-ethoxy-1H-indole-3-carbonitrile

4-nitrophenyl chloroformate

pyridine

→

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

Ausbeute 60.1%

Lösungsmittel

DCE

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis mixture is heated at 75° C. overnight
2. 2
   Waschenis washed with dilute aqueous NaOH
3. 3
   Sonstigeto remove the yellow nitrophenol byproduct
4. 4
   SonstigeThe organic layer is dried
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification by silica gel chromatography (CH2Cl2)

Vorschrift

2-(4-Aminophenyl)-1-cyclobutyl-6-ethoxy-1H-indole-3-carbonitrile (50 mg, 0.15 mmol), prepared as in example 1CM, step B, is combined with 4-nitrophenyl chloroformate (76 mg, 0.38 mmol), DCE (0.5 mL), and pyridine (30 μL, 0.37 mmol). This suspension is stirred at room temperature for 1 h. Rac-cyclopropyl methyl carbinol (100 μL, 0.98 mmol) is added. This mixture is heated at 75° C. overnight. The reaction mixture is then diluted in CH2Cl2 and is washed with dilute aqueous NaOH to remove the yellow nitrophenol byproduct. The organic layer is dried and concentrated. Purification by silica gel chromatography (CH2Cl2) yields rac-[4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester (40 mg, 60%) as a white solid.

Quelle