新产品编号:117577

Chemical Name: 3-Chloro-4-[1-(4-phenoxybenzyl)-1H-indol-5-yloxy]benzoic acid
CAS No. 170146-86-8
项目整合开发状态: Preclinical
项目研究机构: Yamanouchi (Originator)
合成路线:The N-benzyl indole derivative (III) was prepared by alkylation of 5-(benzyloxy)indole (I) with benzyl bromide (II) in the presence of KOH.The O-benzyl protecting group of (III) was subsequently removed by transfer hydrogenolysis with ammonium formate and Pd/C to afford the 5-hydroxyindole (IV),which was further condensed with 3-chloro-4-fluorobenzonitrile (V) to produce the diaryl ether (VI).Finally,basic hydrolysis of the cyano group of (VI) gave the corresponding benzoic acid.

合成路线:The acylation of 5-(benzyloxy)indole (I) with ethyl chloroformate produced the N-(ethoxycarbonyl)indole (II),which was debenzylated by transfer hydrogenolysis with ammonium formate in the presence of Pd/C to afford the 5-hydroxyindole (III).Condensation of (III) with 3-chloro-4-fluorobenzonitrile (IV) produced the diaryl ether (V).Then,basic hydrolysis of the cyano and ethoxycarbonyl groups of (V) gave the benzoic acid derivative (VI).Finally,N-alkylation of the indole ring of (VI) with 4-phenoxybenzyl bromide (VII) furnished the title compound.