2-Amino-5-methylpyridine → 6-Methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine

HRID 339554

Reaktionsgleichung

Reaktionsgleichung von HRID 339554
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=O.C(=O)(O)[O-].[Na+]>CCO>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)[N:1]=2)[CH:4]=1

Komponenten

5

Edukt 3

HCID 153482-Amino-5-methylpyridineHCID 668402-Bromo-4'-nitroacetophenoneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 7499176-Methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridineAusbeute 40,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-5-picoline (0.88 g, 8.19 mmol) and 2-bromo-4′-nitroacetophenone (2.0 g, 8.19 mmol) in EtOH (50 ml) was heated under reflux for 17 h. The reaction mixture was allowed to cool and sodium bicarbonate (840 mg, 9.99 mmol) was added and heating was continued for 18 h. On cooling to room temperature, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (1:1 Hexane/EtOAc) to give the title compound (0.84 g, 40%) as a yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 17 h
  3. temperatureto cool
  4. temperatureheating
  5. customthe solvent was removed under reduced pressure
  6. customthe residue was purified by flash chromatography (1:1 Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-7b3f524f606a4c85802e103451f69231
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

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