Water → 4-chloro-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde

HRID 1012522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012522
[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:15]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:15][C:9]1[C:10]([CH:13]=[O:14])=[CH:11][NH:12][C:8]=1[C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 58349828HCID 58349828, Verbindung

Produkt 1

HCID 866239794-chloro-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehydeAusbeute 44,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-(2-Fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (610 mg) was dissolved in N,N-dimethylformamide (20 mL), N-chlorosuccinimide (641 mg) was added and the mixture was stirred at 80° C. for 40 min. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:2→1:1) to give the title compound as a colorless powder (yield 320 mg, 44%).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:2→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-cc8731ee29e347fc939de7fd02ed2999
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977488B2

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