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【结 构 式】

【分子编号】19407

【品名】2-(4-bromophenyl)acetyl chloride

【CA登记号】

【 分 子 式 】C8H6BrClO

【 分 子 量 】233.49174

【元素组成】C 41.15% H 2.59% Br 34.22% Cl 15.18% O 6.85%

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:(II)

Acid chloride (II) (prepared from 4-bromophenylacetic acid (I) and SOCl2), was condensed with ethyl isobutyrylacetate (III) in the presence of NaH in toluene to yield diketoester (IV). Further reaction of (IV) with hydrazine monohydrate in AcOH gave pyrazole (V). The subsequent N-alkylation of (V) with propyl iodide and NaH provided a 3:1 mixture of regioisomers (VI) and (VII), which were separated by silica gel chromatography. The major isomer (VI) was coupled with arylboronic acid (VIII) in the presence of CsF and Pd(PPh3)4 to provide biphenyl compound (IX). The title compound was then obtained by simultaneous cleavage of the ethyl ester and the N-trityl group on heating with hydroethanolic KOH.

1 Almansa, C.; Gonzales, C.; Torres, M.C.; Carceller, E.; Bartroli, J. (J. Uriach & Cia., SA); New pyrazole derivs. as angiotensin II antagonists. EP 0721454; ES 2105939; JP 1997504804; WO 9604273 .
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) 14247 2-(4-Bromophenyl)acetic acid; p-Bromophenylacetic acid; 4-Bromophenylacetic acid 1878-68-8 C8H7BrO2 详情 详情
(II) 19407 2-(4-bromophenyl)acetyl chloride C8H6BrClO 详情 详情
(III) 19408 ethyl 4-methyl-3-oxopentanoate 7152-15-0 C8H14O3 详情 详情
(IV) 19409 ethyl 2-[2-(4-bromophenyl)acetyl]-4-methyl-3-oxopentanoate C16H19BrO4 详情 详情
(V) 19410 ethyl 5-(4-bromobenzyl)-3-isopropyl-1H-pyrazole-4-carboxylate C16H19BrN2O2 详情 详情
(VI) 19411 ethyl 5-(4-bromobenzyl)-3-isopropyl-1-propyl-1H-pyrazole-4-carboxylate C19H25BrN2O2 详情 详情
(VII) 19412 ethyl 3-(4-bromobenzyl)-5-isopropyl-1-propyl-1H-pyrazole-4-carboxylate C19H25BrN2O2 详情 详情
(VIII) 19413 2-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)phenylboronic acid C26H21BN4O2 详情 详情
(IX) 19414 ethyl 3-isopropyl-1-propyl-5-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-pyrazole-4-carboxylate C45H44N6O2 详情 详情
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