反应 #9563

反应方程式

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

溶剂

n-propanol

water

反应条件

后处理

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

实验过程

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.

来源