Sodium Azide → 5-Azidomethyl-2-fluoro-4-iodo-pyridine

HRID 561008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561008
Br[CH2:2][C:3]1[C:4]([I:10])=[CH:5][C:6]([F:9])=[N:7][CH:8]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[N:11]([CH2:2][C:3]1[C:4]([I:10])=[CH:5][C:6]([F:9])=[N:7][CH:8]=1)=[N+:12]=[N-:13]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 66674459HCID 66674459, Verbindung

Produkt 1

HCID 866404905-Azidomethyl-2-fluoro-4-iodo-pyridineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Combine 5-bromomethyl-2-fluoro-4-iodo-pyridine (0.45 g, 1.4 mmol), sodium azide (370 mg, 5.7 mmol), and 18-crown ether (45 mg, 0.17 mml) in dimethylformamide (10 mL) in a round bottom flask. Stir the mixture for 4 hours at room temperature. Dilute the reaction mixture with chloroform, and wash with water and saturated aqueous sodium chloride. Separate the organic layer from the aqueous layer and dry over MgSO4. After filtration, evaporate the organic solvent in vacuo to give a crude product. Purify the crude with flash column chromatography (eluted with 20% methyl acetate in hexane) to give the title compound (colorless oil, 0.0.32 g, 82%). MS (ES) m/z 279 [M+1]+

Aufarbeitung

  1. washwash with water and saturated aqueous sodium chloride
  2. customSeparate the organic layer from the aqueous layer
  3. dry with materialdry over MgSO4
  4. filtrationAfter filtration
  5. customevaporate the organic solvent in vacuo
  6. customto give a crude product
  7. customPurify the crude
  8. washwith flash column chromatography (eluted with 20% methyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-92ab2a9985944f2994d071ea3e6e62a5
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063212B2

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