Triethylamine → 2-Cyano-3-fluoropyridine

HRID 887638

Reaktionsgleichung

Reaktionsgleichung von HRID 887638
[F:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.C[Si]([C:13]#[N:14])(C)C.C(N(CC)CC)C>CC#N>[F:1][C:2]1[C:3]([C:13]#[N:14])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 123084Pyridine, 3-fluoro-, 1-oxide

Produkt 1

HCID 70604082-Cyano-3-fluoropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The mixture of 3-fluoro-pyridine 1-oxide (0.99 g, 8.75 mmol), trimethylsilyl cyanide (4.80 ml, 35.0 mmol), and triethyl amine (1.84 ml, 13.2 mmol) in 100 ml of CH3CN was heated at reflux overnight. The solvents were removed, under reduced pressure and the residue was partitioned between EtOAc and saturated NaHCO3. The organic portion was separated, dried with Na2SO4, filtered, condensed, the crude compound as purified by flash column chromatography (10 to 20% of EtOAc in hexanes). The titled compound was obtained as a light yellowish solid. MS (ES+): 123.1 (M+H)+. Calc'd for C6H3FN2—122.10.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solvents were removed, under reduced pressure
  4. customthe residue was partitioned between EtOAc and saturated NaHCO3
  5. customThe organic portion was separated
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customcondensed
  9. customthe crude compound as purified by flash column chromatography (10 to 20% of EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e568494b6bbb429ab93068d83e27aa88
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247430B2

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