Chlorosuccinimide → HCID 58365133, Verbindung

A mixture of (S)-4-(3-hydroxypyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (140 mg, 0.34 mmol) and N-chlorosuccinimide (137 mg, 1.02 mmol) in acetonitrile (1.3 mL) and isopropyl alcohol (0.4 mL) was stirred at 35° C. for 5 hours. The cooled reaction mixture was quenched with saturated aqueous sodium thiosulfate (1 mL), 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 solid, which was used in the next step without any further purification (100 mg).

1. customThe cooled reaction mixture
2. customwas quenched with saturated aqueous sodium thiosulfate (1 mL)
3. additiondiluted with ethyl acetate (50 mL)
4. washwashed with water (20 mL)
5. customThe organic layer was separated
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. custompurified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane)

ORD-Eintrag

ord-550be6cad23d4367a1130999d7a98953

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09440976B2