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

Temperature

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 record

ord-f56c0f70681647b9a1b713e17f6db536

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07598382B2