反应 #9519

反应方程式

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

pyridine-3-boronic acid

pyridine-3-boronic acid

→

4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide

收率 53.9%

反应条件

后处理

1. 1
   温度The reaction was heated
2. 2
   workup.ADDITIONwas added
3. 3
   温度the reaction was heated for an additional five hours
4. 4
   其他The crude product was purified by column chromatography on silica gel (
5. 5
   洗涤eluting with chloroform
6. 6
   其他CMA in a gradient from 100:0 to 80:20) and then triturated with methanol
7. 7
   其他isolated by filtration
8. 8
   其他dried for 20 hours under high vacuum at 140° C.

实验过程

4-Methoxybenzyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (1.16 g, 2.0 mmol) and pyridine-3-boronic acid (0.30 g, 2.4 mmol) were coupled according to the method described in Part J of Example 1. The reaction was heated at reflux for 14 hours, at which time additional pyridine-3-boronic acid (0.3 equivalent) was added and the reaction was heated for an additional five hours. The work-up procedure used in Part F of Examples 125–135 was followed. The crude product was purified by column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 100:0 to 80:20) and then triturated with methanol, isolated by filtration, and dried for 20 hours under high vacuum at 140° C. to provide 0.62 g of 4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide as a beige powder, mp 230–231.5° C.

来源