Reaktion #88557

Reaktionsgleichung

(S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)pyrrolidin-3-yl(ethyl)carbamate

Selectfluor

→

title compound

(S)-tert-butyl 1-(3-fluoro-6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)pyrrolidin-3-yl(ethyl)carbamate

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooled reaction mixture
2. 2
   Sonstigewas quenched with saturated aqueous sodium thiosulfate
3. 3
   workup.ADDITIONdiluted with ethyl acetate (50 mL)
4. 4
   Waschenwashed with water (20 mL)
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigepurified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane)

Vorschrift

A mixture of (S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)pyrrolidin-3-yl(ethyl)carbamate (290 mg, 0.54 mmol) and Selectfluor™ (957 mg, 2.7 mmol) in acetonitrile (4.5 mL) was stirred at 0° C. for 5 minutes. The cooled reaction mixture was quenched with saturated aqueous sodium thiosulfate, diluted with ethyl acetate (50 mL), and washed with water (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane) to afford the title compound as a pale yellow foam, which was used in the next step without any further purification (120 mg).

Quelle