N-Iodosuccinimide → 4-Chloro-5-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 1522021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522021
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[I:12]N1C(=O)CCC1=O>CN(C)C=O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[C:11]([I:12])[C:3]=12

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 497616114-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine

Produkt 1

HCID 497616274-Chloro-5-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine (1.8 g, 10.5 mmol) in N,N-dimethylformamide (25 mL) at 0° C. was added N-iodosuccinimide (2.37 g, 10.55 mmol). The mixture was slowly brought to room temperature, quenched with brine and extracted with ethyl acetate (twice). The organic phase was concentrated and purified by column chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound. MS (ESI+) m/z 297 (M+H)+.

Aufarbeitung

  1. customwas slowly brought to room temperature
  2. customquenched with brine
  3. extractionextracted with ethyl acetate (twice)
  4. concentrationThe organic phase was concentrated
  5. custompurified by column chromatography (silica gel, 30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-079cd6b40ffa4f1a8cab8042b6f6ecc9
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073922B2

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