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

Temperatur

120 °C

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.

1. customA thick walled glass tube, equipped with magnetic stir-bar
2. customThe tube was purged with nitrogen
3. customsealed
4. temperatureto cool
5. concentrationconcentrated under reduced pressure
6. customThe solid residue was partitioned between dichloromethane and water
7. additionthe mixture was adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide
8. customThe organic layer was separated
9. custompurified by flash chromatography on silica gel (
10. washeluting with chloroform
11. custommethanol in a gradient from 100:0 to 90:10) followed by recrystallization from acetonitrile

ORD-Eintrag

ord-02f3772b166949dc9620d2ef20591eba

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07091214B2