2-Bromo-1-(4-fluorophenyl)ethan-1-one → 8-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridine

HRID 456689

Reaktionsgleichung

Reaktionsgleichung von HRID 456689
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=O.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:8][C:7]1[C:2]2[N:3]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:1]=2)[CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 516892Sodium BicarbonateHCID 6932672-Amino-3-chloropyridine

Produkt 1

HCID 179762858-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridineAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-3-chloropyridine (6.51 g, 51 mmol) and 2-bromo-4′-fluoroacetophenone (13.0 g, 60 mmol) in ethanol (100 mL) was added sodium bicarbonate (4.91 g, 60 mmol) and the reaction mixture was heated at reflux for 6 hours. The resulting mixture was concentrated to a solid in vacuo. This residue was dissolved in ethyl acetate and the organic phase was washed with water and an aqueous sodium chloride solution. The organic phase was dried (magnesium sulfate), filtered through a silica gel pad and concentrated to give a solid. This solid was recrystallized from acetonitrile, to give 10.1 g (80%) 8-chloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridine as a solid. 1H NMR (CDCl3): δ 8.06 (d, 1H), 7.96 (q, 2H), 7.86 (s, 1H), 7.25 (d, 1H), 7.13 (t, 2H), 6.73 (t, 1H); 19F NMR (CDCl3) δ −114.0; MS m/z 247 (M+1).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe resulting mixture was concentrated to a solid in vacuo
  4. dissolutionThis residue was dissolved in ethyl acetate
  5. washthe organic phase was washed with water
  6. dry with materialThe organic phase was dried (magnesium sulfate)
  7. filtrationfiltered through a silica gel pad
  8. concentrationconcentrated
  9. customto give a solid
  10. customThis solid was recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-33ba5224952445338ce4fa3525dc4b22
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186714B2

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