Sodium hydride → 5-(2-fluoropyridin-3-yl)-1-(2-furylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 1426658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426658
[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.[H-].[Na+].C1OCCOCCOCCOCCOC1.[O:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[S:37](Cl)(=[O:39])=[O:38]>O1CCCC1.C(=O)([O-])O.[Na+]>[F:1][C:2]1[C:7]([C:8]2[N:12]([S:37]([C:33]3[O:32][CH:36]=[CH:35][CH:34]=3)(=[O:39])=[O:38])[CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 2795072Furan-2-sulfonyl ChlorideHCID 58349828HCID 58349828, Verbindung

Produkt 1

HCID 866239765-(2-fluoropyridin-3-yl)-1-(2-furylsulfonyl)-1H-pyrrole-3-carbaldehydeAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (220 mg) in tetrahydrofuran (30 mL) was added sodium hydride (60% in oil, 84 mg) at room temperature and the mixture was stirred for 10 min. 15-Crown-5 (464 mg) was added dropwise, and the mixture was stirred for 5 min. Furan-2-sulfonyl chloride (263 mg) was added, and the mixture was further stirred for 30 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1) and crystallized from diethyl ether to give the title compound as colorless crystals (yield 280 mg, 83%).

Aufarbeitung

  1. stirringthe mixture was stirred for 5 min
  2. stirringthe mixture was further stirred for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1)
  8. customcrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-edc118d5cc464276a0a1b5c9e47714c5
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933105B2

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