تفاعل #9599

معادلة التفاعل

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

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىA thick walled glass tube, equipped with magnetic stir-bar
2. 2
   أخرىThe tube was purged with nitrogen
3. 3
   أخرىsealed
4. 4
   درجة الحرارةto cool
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىThe 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
   أخرىThe organic layer was separated
9. 9
   أخرىpurified by flash chromatography on silica gel (
10. 10
    غسيلeluting with chloroform
11. 11
    أخرىmethanol in a gradient from 100:0 to 90:10) followed by recrystallization from acetonitrile

الإجراء التجريبي

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.

المصدر