반응 #339787

반응 방정식

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

수율 60.1%

용매

DCE

CH2Cl2

반응 조건

후처리

1. 1
   온도This mixture is heated at 75° C. overnight
2. 2
   세척is washed with dilute aqueous NaOH
3. 3
   기타to remove the yellow nitrophenol byproduct
4. 4
   기타The organic layer is dried
5. 5
   농축concentrated
6. 6
   기타Purification by silica gel chromatography (CH2Cl2)

실험 절차

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.

출처