Sodium Carbonate → 7-[2-{6-(4-Methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-azepan-2-one

Participants

Reaction Steps

The title compound is 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), 677 μl of aqueous sodium carbonate solution (strength 2.0 M), 52 mg of commercially available 4-methoxyphenylboronic acid, and 72 mg of trans-dichloro-bis(tricyclohexyl-phosphine)-palladium(II) at 110° C. for 96 hours. Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-20 vol. % ethanol) yields 99 mg of the title compound as a waxy solid. ESI-MS: 365.2 (MH+). TLC: Rf=0.32 (dichloromethane/ethanol 10:1 parts by volume).

Provenance & Evidence