Reacción #88541

Ecuación de reacción

iodoethane

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

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with water (30 μL)
2. 2
   workup.ADDITIONdiluted with ethyl acetate (50 mL)
3. 3
   Lavadowashed with water (20 mL)
4. 4
   OtroThe organic layer was separated
5. 5
   Secadodried over sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otropurified by flash chromatography (silica, 4 g, ISCO, 0-60% ethyl acetate in heptane)

Procedimiento

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)piperidin-3-ylcarbamate (130 mg, 0.25 mmol) in tetrahydrofuran (2 mL) was added sodium hydride as a 60% dispersion in mineral oil (20 mg, 0.5 mmol) followed by iodoethane (0.06 mL, 0.75 mmol) and reaction mixture was stirred overnight at ambient temperature. The reaction was quenched with water (30 μL), 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, 0-60% ethyl acetate in heptane) to afford the title compound as a colorless oil, which was used in the next step without any further purification (90 mg).

Fuente