Sodium Azide → 2-(Azidomethyl)-6-bromopyridine

HRID 2060603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060603
[N-:1]=[N+:2]=[N-:3].[Na+].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12]Br)[N:7]=1>CS(C)=O.O>[N:1]([CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([Br:5])[N:7]=1)=[N+:2]=[N-:3]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 129547962-Bromo-6-(bromomethyl)pyridine

Produkt 1

HCID 453574032-(Azidomethyl)-6-bromopyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium azide (3.11 g, 47.8 mmol) and 2-bromo-6-(bromomethyl)pyridine (4.00 g, 15.94 mmol) were combined in DMSO (30 mL) and stirred at room temperature for 4 h. The mixture was subsequently diluted with water and extracted with diethyl ether (2×). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated. The residue was purified by flash chromatography (0-10% EtOAc/hexanes) to yield the title compound as a colorless oil. LRMS (APCI) calc'd for C6H6BrN4 [M+H]+: 213, Found: 213.

Aufarbeitung

  1. extractionextracted with diethyl ether (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (0-10% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-77eb3e09aee54644a952788274b754c7
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278335B2

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