3-Nitropyridin-2-ylamine → 2-(4-Fluorophenyl)-8-nitroimidazo[1,2-a]pyridine

HRID 456683

Reaktionsgleichung

Reaktionsgleichung von HRID 456683
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=O>CN(C)C=O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[N:1]=[C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]3[CH:12]=2)=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 778873-Nitropyridin-2-ylamineHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Produkt 1

HCID 179762862-(4-Fluorophenyl)-8-nitroimidazo[1,2-a]pyridineAusbeute 36,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-3-nitropyridine (1.3 g, 9.3 mmol) in N,N-dimethylformamide (20 mL) was added 2-bromo-4′-fluoroacetophenone (2 g, 9.3 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 dichloromethane and the organic phase was washed with aqueous sodium bicarbonate 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 methanol to give 870 mg (36%) of 2-(4-fluorophenyl)-8-nitroimidazo[1,2-α]pyridine as a brown solid. 1H NMR (d6-DMSO): δ 8.98 (d, 1H), 8.69 (s,1H), 8.32 (d, 1H), 8.10 (q, 2H), 7.36 (t, 2H), 7.15 (t, 1H); 19F NMR (DMSO-d6) δ −113.7; MS m/z 258 (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 dichloromethane
  5. washthe organic phase was washed with aqueous sodium bicarbonate
  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 methanol

Quellen und Nachweise

ORD-Eintrag
ord-55a334e591de4e1187675bab72ccfefd
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186714B2

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