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【结 构 式】

【分子编号】64423

【品名】4-[4-(2-bromoethoxy)phenyl]-3-butyn-1-ol

【CA登记号】

【 分 子 式 】C12H13BrO2

【 分 子 量 】269.13802

【元素组成】C 53.55% H 4.87% Br 29.69% O 11.89%

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:(V)

4-Iodophenol (I) is alkylated with 1,2-dibromoethane (II) to afford 1-(2-bromoethoxy)-4-iodobenzene (III). Subsequent palladium-catalyzed coupling of aryl iodide (III) with 3-butyn-1-ol (IV) furnishes the phenylbutynol adduct (V), which is further hydrogenated in the presence of Pd/C to the saturated alcohol (VI). Condensation of the alkyl bromide (VI) with (R)-p-chlorobenzhydrylpiperazine (VII) produces the dialkylated piperazine (VIII). Then, Mitsunobu coupling of arylbutanol (VIII) with phenoxycarbonylaminophenoxyformate (IX) leads to the protected hydroxamic acid (X). This is finally treated with methanolic ammonia to provide the title N-hydroxyurea derivative.

1 Chatelain, P.; Differding, E.; Cai, X.; Hussoin, S.; Grewal, G.; Young, M.; Lewis, T.; Toy-Palmer, A.; Scannel, R.; Ellis, J.; Lassoie, M.-A. (UCB SA); Cpds. and methods for treatment of asthma, allergy and inflammatory disorders. JP 2002540198; US 6451801; WO 0058295 .
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) 22242 4-iodophenol 540-38-5 C6H5IO 详情 详情
(II) 10252 1,2-Dibromoethane; Ethylene dibromide 106-93-4 C2H4Br2 详情 详情
(III) 64422 1-(2-bromoethoxy)-4-iodobenzene; 2-bromoethyl 4-iodophenyl ether C8H8BrIO 详情 详情
(IV) 32507 3-butyn-1-ol 927-74-2 C4H6O 详情 详情
(V) 64423 4-[4-(2-bromoethoxy)phenyl]-3-butyn-1-ol C12H13BrO2 详情 详情
(VI) 64424 4-[4-(2-bromoethoxy)phenyl]-1-butanol C12H17BrO2 详情 详情
(VII) 30404 1-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazine C17H19ClN2 详情 详情
(VIII) 64425 4-[4-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]-1-piperazinyl}ethoxy)phenyl]-1-butanol C29H35ClN2O2 详情 详情
(IX) 19646 1-[([[(phenoxycarbonyl)oxy]amino]carbonyl)oxy]benzene C14H11NO5 详情 详情
(X) 64426 1-[(R)-(4-chlorophenyl)(phenyl)methyl]-4-{2-[4-(4-{(phenoxycarbonyl)[(phenoxycarbonyl)oxy]amino}butyl)phenoxy]ethyl}piperazine C43H44ClN3O6 详情 详情
Extended Information