2-Butanone, 3-bromo- → 2,3-Dimethyl-8-(2-ethyl-6-methylbenzyloxy)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427496
[NH2:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:20][CH3:21])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.Br[CH:23]([CH3:27])[C:24](=O)[CH3:25].C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:27][C:23]1[N:1]=[C:2]2[C:10]([O:11][CH2:12][C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:20][CH3:21])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]2[C:24]=1[CH3:25]

Komponenten

5

Edukt 3

HCID 131422-Butanone, 3-bromo-HCID 516892Sodium BicarbonateHCID 183574336-Amino-5-(2-ethyl-6-methylbenzyloxy)nicotinamide

Produkt 1

HCID 98191772,3-Dimethyl-8-(2-ethyl-6-methylbenzyloxy)-imidazo[1,2-a]pyridine-6-carboxamideAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

6-amino-5-(2-ethyl-6-methylbenzyloxy)nicotinamide (0.14 g, 0.49 mmol), 3-bromo-2-butanone (0.075 g, 0.49 mmol) and sodium bicarbonate (0.1 g, 1.2 mmol) was added to acetonitrile (3 ml) and was refluxed for 20 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent. Crystallization from acetonitrile gave 0.058 g (35%) of the title compound.

Aufarbeitung

  1. temperaturewas refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel
  4. customCrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-8b60a32ff297408e940b6e3bfa71a9f6
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313137B1

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