反应 #1797567

反应方程式

7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one

compound B1

7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one

7-[2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one

compound C1

7-[2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one

sodium carbonate

1-ethyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonyl]-piperazine

compound C4

1-ethyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonyl]-piperazine

→

title compound

7-(2-{6-[4-(4-Ethyl-piperazine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-azepan-2-one

反应条件

后处理

1. 1
   其他200 ml of dichloromethane and 75 ml of water, purification by chromatography on flash silica gel (eluent gradient dichloromethane/5-50 vol. % ethanol)

实验过程

The title compound is analogously synthesized as described for 7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound B1) from 300 mg of 7-[2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound C1), 2.67 ml of aqueous sodium carbonate solution (strength 2.0 M), 510 mg 1-ethyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonyl]-piperazine (compound C4), and 131 mg of trans-dichloro-bis(tricyclohexyl-phosphine)-palladium(II) at 110° C. for 18 hours. After aqueous work-up using 200 ml of dichloromethane and 75 ml of water, purification by chromatography on flash silica gel (eluent gradient dichloromethane/5-50 vol. % ethanol) yields 175 mg of the title compound as a waxy solid. ESI-MS: 511.3 (MH+). TLC: Rf=0.30 (dichloromethane/ethanol 8:1 parts by volume).

来源