N-bromobutanimide → N-(3-Bromo-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide

HRID 1971616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971616
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]([F:25])([F:24])[C:11]([NH:13][C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]2[CH:23]=1)=[O:12]>C(#N)C>[Br:1][C:23]1[N:17]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]2=[N:15][C:14]=1[NH:13][C:11](=[O:12])[C:10]([F:24])([F:9])[F:25]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 251966492,2,2-Trifluoro-N-(6-fluoroimidazo[1,2-a]pyridin-2-yl)acetamide2×

Produkt 1

HCID 57607463N-(3-Bromo-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (2.96 g, 0.0166 mol) was added to a solution of 2,2,2-Trifluoro-N-(6-fluoro-imidazo[1,2-a]pyridin-2-yl)-acetamide (compound c, 3.74 g, 0.0151 mol) in acetonitrile (70 mL) and stirred at room temperature. The reaction mixture was stirred at room temperature for 15 minutes. Reaction mixture was concentrated under reduced pressure, crude product taken up in ethyl acetate, washed with water, organic layer collected, dried over Na2SO4, concentrated in vacuo and crude product purified by column chromatography (50% ethyl acetate/hexanes) to give product as an off white solid. Rf 0.47, 50% ethyl acetate/hexanes; MS m/z 327 (M+H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 15 minutes
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure, crude product
  4. washwashed with water, organic layer
  5. customcollected
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo and crude product
  8. custompurified by column chromatography (50% ethyl acetate/hexanes)
  9. customto give product as an off white solid

Quellen und Nachweise

ORD-Eintrag
ord-7549f0a8df434ba9abec28a002c38702
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431608B2

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