Reaktion #1905396

Reaktionsgleichung

Triethylamine

potassium vinyltrifluoroborate

7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

sodium hydroxide

→

1-(2-methylpropyl)-2-propyl-7-vinyl-1H-imidazo[4,5-c]quinolin-4-amine

Lösungsmittel

n-propanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturat reflux under a nitrogen atmosphere until it
3. 3
   Sonstige(between four and 18 hours)
4. 4
   ExtraktionThe mixture was extracted with ethyl acetate
5. 5
   Filtrationthe combined organic fractions were filtered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe crude product was purified by flash column chromatography on silica gel (
8. 8
   Wascheneluting with chloroform
9. 9
   Sonstigemethanol in a gradient from 100:0 to 90:10), followed by recrystallization from acetonitrile

Vorschrift

Triethylamine (3.0 equivalents), potassium vinyltrifluoroborate (1.0 equivalent) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.2 equivalent) were added to a solution of 7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (1.0 equivalent) in n-propanol (30 ml/g). The reaction mixture was heated at reflux under a nitrogen atmosphere until it was complete (between four and 18 hours) and then poured into water (3 volumes). The pH of the mixture was monitored and adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide if needed. The mixture was extracted with ethyl acetate, and the combined organic fractions were filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (eluting with chloroform:methanol in a gradient from 100:0 to 90:10), followed by recrystallization from acetonitrile to provide 1-(2-methylpropyl)-2-propyl-7-vinyl-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid.

Quelle