반응 #9599

반응 방정식

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

용매

toluene

반응 조건

후처리

1. 1
   기타A thick walled glass tube, equipped with magnetic stir-bar
2. 2
   기타The tube was purged with nitrogen
3. 3
   기타sealed
4. 4
   온도to cool
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The 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
   기타The organic layer was separated
9. 9
   기타purified by flash chromatography on silica gel (
10. 10
    세척eluting with chloroform
11. 11
    기타methanol in a gradient from 100:0 to 90:10) followed by recrystallization from acetonitrile

실험 절차

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.

출처