Selectfluor → HCID 59255049, Verbindung

HRID 639546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639546
[CH:1]([N:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]1=[O:16])([CH3:3])[CH3:2].[F:17][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>C(#N)C>[F:17][C:8]1[CH:7]=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5](=[O:16])[N:4]([CH:1]([CH3:2])[CH3:3])[C:9]=1[CH3:10]

Komponenten

4

Edukt 2

HCID 2724933SelectfluorHCID 59255053HCID 59255053, Verbindung

Produkt 1

HCID 59255049HCID 59255049, VerbindungAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of ethyl 1-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate as prepared in Example 1(5) (2.23 g, 10.0 mmol) and 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (3.76 g, 10.6 mmol) in acetonitrile (80 mL) was stirred at room temperature for 16 h. The mixture was quenched with water (300 mL), and extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with water (100 mL×6), brine (100 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=2/1˜1/1) to give 572 mg (24%) of the title compound as a yellow solid.

Aufarbeitung

  1. customThe mixture was quenched with water (300 mL)
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. washThe combined organic layers were washed with water (100 mL×6), brine (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=2/1˜1/1)

Quellen und Nachweise

ORD-Eintrag
ord-7b51e75258474c1e828e4ef44652948b
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691881B2

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