3-Nitropyridine → 6-Azaindole

HRID 392132

Reaktionsgleichung

Reaktionsgleichung von HRID 392132
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH:10]([Mg]Br)=[CH2:11]>C1COCC1>[NH:1]1[C:4]2[C:9](=[CH:8][CH:7]=[N:6][CH:5]=2)[CH:11]=[CH:10]1

Komponenten

4

Edukt 2

HCID 1376303-NitropyridineHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 92196-Azaindole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of 3-nitropyridine in THF at −78° C. is treated with vinyl magnesium bromide (3 eq), stirred at −20° C. for 8 h and quenched with 20% ammonium chloride. The phases are separated and the aqueous phase is extracted with EtOAc. The organic phase and the combined extracts are mixed together, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed over silica gel to afford the title 6-azaindole.

Aufarbeitung

  1. customquenched with 20% ammonium chloride
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with EtOAc
  4. additionThe organic phase and the combined extracts are mixed together
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-74628ef804be4d30a069d0b6e8947871
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800640B2

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