تفاعل #339787

معادلة التفاعل

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

المردود 60.1%

المذيبات

DCE

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThis mixture is heated at 75° C. overnight
2. 2
   غسيلis washed with dilute aqueous NaOH
3. 3
   أخرىto remove the yellow nitrophenol byproduct
4. 4
   أخرىThe organic layer is dried
5. 5
   تركيزconcentrated
6. 6
   أخرىPurification by silica gel chromatography (CH2Cl2)

الإجراء التجريبي

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.

المصدر