反应详情

2-(4-Aminophenyl)-1-cyclobutyl-6-ethoxy-1H-indole-3-carbonitrile (40 mg, 0.12 mmol), prepared as in example 1CM, step B, is combined with 4-nitrophenyl chloroformate (60 mg, 0.30 mmol), CH2Cl2 (400 μL), and pyridine (25 μL, 0.31 mmol). This suspension is stirred at room temperature for 1 hour. Ethanolamine (42 μL, 0.70 mmol) is added. After stirring at room temperature for an additional 30 min, the reaction mixture is diluted in CH2Cl2 and is washed with dilute aqueous NaOH to remove the yellow nitrophenol by-product. The organic layer is dried and concentrated. Purification by silica gel chromatography (CH2Cl2/Acetone, 7/3) yields 1-[4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-3-(2-hydroxy-ethyl)-urea (40 mg, 80%) as a white solid.

1. stirringAfter stirring at room temperature for an additional 30 min
2. washis washed with dilute aqueous NaOH
3. customto remove the yellow nitrophenol by-product
4. customThe organic layer is dried
5. concentrationconcentrated
6. customPurification by silica gel chromatography (CH2Cl2/Acetone, 7/3)