Reaktion #88552

Reaktionsgleichung

iodoethane

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

sodium hydride

→

title compound

(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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with water (0.1 mL)
2. 2
   workup.ADDITIONdiluted with ethyl acetate (100 mL)
3. 3
   Waschenwashed with water (50 mL)
4. 4
   SonstigeThe organic layer was separated
5. 5
   Trocknendried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigepurified by flash chromatography (silica, 4 g, ISCO, 0-60% ethyl acetate in heptane)

Vorschrift

To a solution 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-ylcarbamate (700 mg, 1.0 mmol) in tetrahydrofuran (11 mL) was added sodium hydride as a 60% dispersion in mineral oil (140 mg, 3.4 mmol) followed by iodoethane (0.77 mL, 9.4 mmol) and reaction mixture was stirred overnight at ambient temperature. The reaction was quenched with water (0.1 mL), diluted with ethyl acetate (100 mL) and washed with water (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 4 g, ISCO, 0-60% ethyl acetate in heptane) to afford the title compound as a white solid, which was used in the next step without any further purification (560 mg. 80%).

Quelle