Реакция #11685

Уравнение реакции

hydrochloric acid

sodium methoxide

(S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

bromoacetonitrile

→

title compound

Выход 26.8%

(S)-3-(5-chloroindole-2-carbonylamino)-1-cyanomethyl-3,4-dihydrocarbostyril

Выход 26.8%

Растворители

ethyl acetate

water

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ДругоеAfter cooing to 0° C.
2. 2
   ДругоеThe organic phase was separated
3. 3
   Промывкаwashed with brine
4. 4
   Сушкаdried over anhydrous sodium sulfate
5. 5
   ДругоеAfter solvent evaporation under vacuum
6. 6
   Другоеthe crude product was purified by reverse phase preparative HPLC

Методика

(S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 4, 13.4 mg) was dissolved in tetrahydrofuran (5 mL) at room temperature under argon with stirring. After cooing to 0° C., sodium methoxide (4.3 mg) was added, followed 2 h later by bromoacetonitrile (7.2 mg). This was warmed to room temperature over 2 h, and 2 h later water (15 mL), 1.0 M aqueous hydrochloric acid (1 mL), and ethyl acetate (20 mL) were added. The organic phase was separated, washed with brine, and dried over anhydrous sodium sulfate. After solvent evaporation under vacuum, the crude product was purified by reverse phase preparative HPLC to provide the title compound (4 mg). HPLC/MS [M+H]+, 379; HPLC/MS [M+Na]+, 401.

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