Réaction #9518

Équation de réaction

Dimethyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide

phenyl boronic acid

→

dimethyl 4-[4-amino-2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide

Rendement 20.8%

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was heated
2. 2
   Températureat reflux for 14 hours
3. 3
   AutreThe crude product was recrystallized from methanol
4. 4
   Autrepurified by column chromatography on silica gel (
5. 5
   Lavageeluting with chloroform
6. 6
   AutreThe solid was then purified by HPFC

Mode opératoire

Dimethyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (0.66 g, 1.4 mmol) and phenyl boronic acid (0.20 g, 1.6 mmol) were coupled according to the method described in Part J of Example 1. The reaction was heated at reflux for 14 hours, and the work-up procedure used in Part F of Examples 125–135 was followed. The crude product was recrystallized from methanol and then purified by column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 100:0 to 90:10). The solid was then purified by HPFC to provide 0.14 g of dimethyl 4-[4-amino-2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide as Off-white needles, mp 207–208° C.

Source