Реакция #77798

Уравнение реакции

5-[6-Fluoro-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-5-yl]-pent-4-yn-1-ol

diisopropyl ethylamine

methanesulfonylchloride

HCl

→

Methanesulfonic acid 5-[6-fluoro-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-5-yl]-pent-4-ynyl ester

Выход 94.2%

Растворители

CH2Cl2

Et2O

Условия реакции

Обработка

1. 1
   Сушкаdrying of the organic layer with MgSO4, and evaporation of the solvent

Методика

A solution of 50 mg (0.141 mmol) of 5-[6-Fluoro-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-5-yl]-pent-4-yn-1-ol and 0.072 ml (0.42 mmol) diisopropyl ethylamine in 2 ml CH2Cl2 was treated at 0° C. with 0.033 ml (0.42 mmol) methanesulfonylchloride and stirred at room temperature for one hour. Addition of aqueous 0.1M HCl, extraction with Et2O, drying of the organic layer with MgSO4, and evaporation of the solvent gave 60 mg of Methanesulfonic acid 5-[6-fluoro-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-5-yl]-pent-4-ynyl ester as brown oil of which 12 mg were dissolved in 0.5 ml DMF, treated with 0.043 ml (0.053 mmol) 2-(methylamino)ethanol and stirred at 80° C. during 2 hours. Evaporation of the solvent and excess 2-(methylamino)ethanol and chromatography on silica gel with EtOAc/MeOH/NEt3 10:1:0.1 gave 10 mg (82%) of 2-({5-[6-Fluoro-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-5-yl]-pent-4-ynyl}-methyl-amino)-ethanol as a light yellow oil, MS: 431 (MH+).

Источник