تفاعل #9545

معادلة التفاعل

8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinolin-4-amine

4-vinylpyridine

triphenylphosphine

triethylamine

→

1-(2-methylpropyl)-8-(2-pyridin-4-ylvinyl)-1H-imidazo[4,5-c]-quinolin-4-amine

المردود 65.1%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was removed under reduced pressure
2. 2
   workup.ADDITIONthe residue was adjusted to pH 2 with the addition of concentrated hydrochloric acid
3. 3
   workup.ADDITIONWater was added
4. 4
   ترشيحthe mixture was filtered through a layer of CELITE
5. 5
   ترشيحfilter aid
6. 6
   workup.ADDITIONAqueous sodium carbonate (2 N) was added to the filtrate
7. 7
   استخلاصThe solution was then extracted with dichloromethane
8. 8
   تجفيفthe combined extracts were dried over sodium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated under reduced pressure
11. 11
    أخرىThe crude product was purified by flash column chromatography on silica gel (
12. 12
    غسيلeluting with chloroform

الإجراء التجريبي

Nitrogen was bubbled through a solution of 8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinolin-4-amine (3.0 g, 9.4 mmol), 4-vinylpyridine (2.0 mL, 19 mmol), triphenylphosphine (246 mg, 0.94 mmol), and triethylamine (2.7 mL, 19 mmol) in acetonitrile (50 mL) for 15 minutes. Palladium (II) acetate (105 mg, 0.47 mmol) was added, and the reaction was heated at 100° C. for three days. The solvent was removed under reduced pressure, and the residue was adjusted to pH 2 with the addition of concentrated hydrochloric acid. Water was added, and the mixture was filtered through a layer of CELITE filter aid. Aqueous sodium carbonate (2 N) was added to the filtrate to adjust the solution to pH 10. The solution was then extracted with dichloromethane, and the combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 95:5 to 80:20) to provide 2.1 g of 1-(2-methylpropyl)-8-(2-pyridin-4-ylvinyl)-1H-imidazo[4,5-c]-quinolin-4-amine as a yellow solid.

المصدر