Reacción #331993

Ecuación de reacción

phenyl vinyl sulfide

triethylamine

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-ylamine

→

2-ethoxymethyl-1-(3-isopropoxypropyl)-7-[(E)-2-(phenylthio)ethenyl]-1H-imidazo[4,5-c]quinolin-4-amine hydrobromide

Rendimiento 25.5%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrocap
2. 2
   TemperaturaThe reaction mixture was cooled to ambient temperature
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   OtroThe residue was purified by flash column chromatography (silica gel
5. 5
   Lavadoeluting with a linear gradient of 1-7% methanol in dichloromethane),
6. 6
   Otrofollowed by recrystallization from acetonitrile

Procedimiento

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-ylamine (1.00 g, 2.46 mmol), tris(2-tolyl)phosphine (16 mg, 0.05 mmol) and a stir bar were added to a pressure vessel. Palladium(II) acetate (6 mg, 0.025 mmol), phenyl vinyl sulfide (0.330 mL, 2.53 mmol) and triethylamine (0.685 mL, 4.92 mmol) were subsequently added, followed by toluene (5 mL). The vessel was sealed with a TEFLON cap and the reaction was heated at 110° C. for 40 hours. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, eluting with a linear gradient of 1-7% methanol in dichloromethane), followed by recrystallization from acetonitrile to provide 0.35 g of 2-ethoxymethyl-1-(3-isopropoxypropyl)-7-[(E)-2-(phenylthio)ethenyl]-1H-imidazo[4,5-c]quinolin-4-amine hydrobromide as yellow-orange crystals, mp 220-221° C.

Fuente