反应 #1797565

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

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

compound C1

N,N-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide

compound C2

N,N-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide

→

title compound

N,N-Dimethyl-4-{2-[2-(7-oxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide

溶剂

sodium carbonate

反应条件

后处理

1. 1
   其他(microwave irradiation, power ≦300 W)
2. 2
   其他Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 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 100 mg of 7-[2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound C1), 890 μl of aqueous sodium carbonate solution (strength 2.0 M), 138 mg N,N-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide (compound C2), and 26 mg of trans-dichloro-bis(tricyclohexyl-phosphine)-palladium(II) at 160° C. for 30 min (microwave irradiation, power ≦300 W). Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 vol. % ethanol) yields 93 mg of the title compound as a waxy solid. ESI-MS: 442.4 (MH+). TLC: Rf=0.41 (dichloromethane/ethanol 10:1 parts by volume).

来源