Reaktion #11685

Reaktionsgleichung

hydrochloric acid

sodium methoxide

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

bromoacetonitrile

→

title compound

Ausbeute 26.8%

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

Ausbeute 26.8%

Lösungsmittel

ethyl acetate

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter cooing to 0° C.
2. 2
   SonstigeThe organic phase was separated
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   SonstigeAfter solvent evaporation under vacuum
6. 6
   Sonstigethe crude product was purified by reverse phase preparative HPLC

Vorschrift

(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.

Quelle