ethyl 8-(4'-bromo[1,1'-biphenyl]-4-yl)-8-oxooctanoate -Drug Synthesis Database

【结构式】

【分子编号】55805

【品名】ethyl 8-(4'-bromo[1,1'-biphenyl]-4-yl)-8-oxooctanoate

【CA登记号】

【分子式】C₂₂H₂₅BrO₃

【分子量】417.3427

【元素组成】C 63.32% H 6.04% Br 19.15% O 11.5%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

The reaction of ethyl 7-bromoheptanoate (I) with NaI, Zn, dibromoethane, LiCl and CuCN gives the organometallic derivative (II), which is condensed with 4-bromobenzoyl chloride (III) in THF to yield 8-(4-bromophenyl)-8-oxooctanoic acid ethyl ester (IV). The condensation of (IV) with 4-bromophenylboronic acid (V) by means of Pd(PPh3)4 and K2CO3 in hot toluene affords 8-(4'-bromobiphenyl-4-yl)-8-oxooctanoic acid ethyl ester (VI), which is hydrolyzed with NaOH in THF/methanol to provide the corresponding carboxylic acid (VII). Finally, this compound is treated with hydroxylamine, EDC, HOBt and TEA to obtain the target hydroxamic acid.

参考文献中间体

合成目标

【1】 Woo, S.H.; et al.; Structurally simple trichostatin A-like straight chain hydroxamates as potent histone deacetylase inhibitors. J Med Chem 2002, 45, 13, 2877.
【2】 Delorme, D.; Woo, S.H.; Vaisburg, A. (MethylGene Inc.); Inhibitors of histone deacetylase. WO 0170675 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	36428	ethyl 7-bromoheptanoate	29823-18-5	C₉H₁₇BrO₂	详情	详情
(II)	55802			C₁₀H₁₇CuINO₂Zn	详情	详情
(III)	45960	4-bromobenzoyl chloride	586-75-4	C₇H₄BrClO	详情	详情
(IV)	55803	ethyl 8-(4-bromophenyl)-8-oxooctanoate		C₁₆H₂₁BrO₃	详情	详情
(V)	55804	4-Bromobenzeneboronic acid; 4-Bromophenylboronic acid	5467-74-3	C₆H₆BBrO₂	详情	详情
(VI)	55805	ethyl 8-(4'-bromo[1,1'-biphenyl]-4-yl)-8-oxooctanoate		C₂₂H₂₅BrO₃	详情	详情
(VII)	55806	8-(4'-bromo[1,1'-biphenyl]-4-yl)-8-oxooctanoic acid		C₂₀H₂₁BrO₃	详情	详情

Extended Information