反应详情

温度

80 °C

122 mg of 5-chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-hydroxy-phenyl)-ethyl]-amide (0.25 mmol) and 52 mg potassium carbonate (0.375 mmol) were suspended in 5 ml acetonitrile and treated with 0.027 ml bromomethyl-cyclopropane (0.275 mmol). The mixture was stirred for 24 h in an oil-bath heated to 80° C. After cooling down, the mixture was poured on water/EtOAc, and after separation the aqueous phase was extracted with EtOAc. The combined organic phases were then washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silicagel, heptane/EtOAc 9:1) leading to 66 mg of 5-chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-cyclopropylmethoxy-phenyl)-ethyl]-amide as a colorless viscous oil. MS (ISP) 515.5 (M+H)+.

1. temperatureAfter cooling down
2. additionthe mixture was poured on water/EtOAc
3. customafter separation the aqueous phase
4. extractionwas extracted with EtOAc
5. washThe combined organic phases were then washed with water and brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by column chromatography (8 g silicagel, heptane/EtOAc 9:1)