Реакция #9599

Уравнение реакции

tri-ortho-tolylphosphine

triethylamine

2-vinylpyridine

7-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine

→

(E)-2-ethoxymethyl-1-(3-methoxypropyl)-7-(2-pyridin-2-ylvinyl)-1H-imidazo[4,5-c]quinolin-4-amine

Растворители

toluene

Условия реакции

Обработка

1. 1
   ДругоеA thick walled glass tube, equipped with magnetic stir-bar
2. 2
   ДругоеThe tube was purged with nitrogen
3. 3
   Другоеsealed
4. 4
   Температураto cool
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe solid residue was partitioned between dichloromethane and water
7. 7
   workup.ADDITIONthe mixture was adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide
8. 8
   ДругоеThe organic layer was separated
9. 9
   Другоеpurified by flash chromatography on silica gel (
10. 10
    Промывкаeluting with chloroform
11. 11
    Другоеmethanol in a gradient from 100:0 to 90:10) followed by recrystallization from acetonitrile

Методика

A thick walled glass tube, equipped with magnetic stir-bar, was charged with toluene (20 mL/g), palladium (II) acetate (0.1 equivalents), tri-ortho-tolylphosphine (0.3 equivalents), triethylamine (3.0 equivalents), 2-vinylpyridine (1.0 equivalent), and 7-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.0 eq.). The tube was purged with nitrogen and sealed. The reaction mixture was heated at 120° C. for 24–48 hours. The reaction mixture was allowed to cool and then concentrated under reduced pressure. The solid residue was partitioned between dichloromethane and water, and the mixture was adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide. The organic layer was separated and purified by flash chromatography on silica gel (eluting with chloroform:methanol in a gradient from 100:0 to 90:10) followed by recrystallization from acetonitrile to provide (E)-2-ethoxymethyl-1-(3-methoxypropyl)-7-(2-pyridin-2-ylvinyl)-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid.

Источник