Trifluoroacetic anhydride → 2-Ethyl-6-iodo-3-methylimidazo[1,2-a]pyridine

HRID 2202986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202986
[I:1][C:2]1[CH:3]=[CH:4][C:5](=[N:14]S(C2C=CC(C)=CC=2)(=O)=O)[N:6]([CH:8]([C:10](=O)[CH2:11][CH3:12])[CH3:9])[CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[CH2:11]([C:10]1[N:14]=[C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][N:6]2[C:8]=1[CH3:9])[CH3:12]

Komponenten

4

Edukt 2

HCID 9845Trifluoroacetic anhydrideHCID 131735782N-(5-Iodo-1-(3-oxopentan-2-yl)pyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide

Produkt 1

HCID 231582522-Ethyl-6-iodo-3-methylimidazo[1,2-a]pyridineAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of N-(5-iodo-1-(3-oxopentan-2-yl)pyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide (4 g) in THF (50 ml) was added trifluoroacetic anhydride (10 ml) at 0° C., and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo, poured into saturated aqueous NaHCO3 solution and extracted with DCM. The extract was washed with brine, dried over Na2SO4, concentrated in vacuo, and purified by silica gel column chromatography (hexane/EtOAc) to afford the title compound (1.3 g) as a yellow solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionpoured into saturated aqueous NaHCO3 solution
  3. extractionextracted with DCM
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel column chromatography (hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6432f6fd9d8748f19642b869821a16d5
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365540B2

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