反応 #9563

反応方程式

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

溶媒

n-propanol

water

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度at reflux under a nitrogen atmosphere until it
3. 3
   その他(between four and 18 hours)
4. 4
   抽出The mixture was extracted with ethyl acetate
5. 5
   ろ過the combined organic fractions were filtered
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The crude product was purified by flash column chromatography on silica gel (
8. 8
   洗浄eluting with chloroform
9. 9
   その他methanol in a gradient from 100:0 to 90:10), followed by recrystallization from acetonitrile

実験手順

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.

出典