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【结 构 式】

【分子编号】43330

【品名】2,6-dichloro-N-hydroxybenzenecarboximidoyl chloride

【CA登记号】

【 分 子 式 】C7H4Cl3NO

【 分 子 量 】224.473

【元素组成】C 37.46% H 1.8% Cl 47.38% N 6.24% O 7.13%

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:(III)

2,6-Dichlorobenzaldehyde (I) was converted to oxime (II) and then chlorinated with N-chlorosuccinimide to afford the oximidoyl chloride (III). The cycloaddition reaction between ketoester (IV) and the nitrile oxide resulting from (III) in the presence of NaOMe gave rise to the isoxazole system (V). The ester group of (V) was then reduced to alcohol (VI) employing diisobutylaluminium hydride. Subsequent coupling of alcohol (VI) with 2-chloro-4-hydroxybenzaldehyde (VII) under Mitsunobu conditions provided ether (VIII). Phosphonate (X) was prepared by heating methyl 3-(bromomethyl)benzoate (IX) with triethyl phosphite at 185 C. Horner-Emmons condensation of aldehyde (VIII) with phosphonate (X) in the presence of NaH in THF furnished the stilbene derivative (XI). The methyl ester group of (XI) was finally hydrolyzed by means of LiOH in aqueous THF.

1 Lehmann, J.; Stimmel, J.B.; Blanchard, S.G.; Kliewer, S.A.; Willson, T.M.; Parks, D.J. (Glaxo Group Ltd.); Assays for ligands for nuclear receptors. WO 0037077 .
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) 27507 2,6-dichlorobenzaldehyde 83-38-5 C7H4Cl2O 详情 详情
(II) 43329 2,6-dichlorobenzaldehyde oxime C7H5Cl2NO 详情 详情
(III) 43330 2,6-dichloro-N-hydroxybenzenecarboximidoyl chloride C7H4Cl3NO 详情 详情
(IV) 43331 methyl 4-methyl-3-oxopentanoate 42558-54-3 C7H12O3 详情 详情
(V) 43332 methyl 3-(2,6-dichlorophenyl)-5-isopropyl-4-isoxazolecarboxylate C14H13Cl2NO3 详情 详情
(VI) 43333 [3-(2,6-dichlorophenyl)-5-isopropyl-4-isoxazolyl]methanol C13H13Cl2NO2 详情 详情
(VII) 43334 2-chloro-4-hydroxybenzaldehyde C7H5ClO2 详情 详情
(VIII) 43335 2-chloro-4-[[3-(2,6-dichlorophenyl)-5-isopropyl-4-isoxazolyl]methoxy]benzaldehyde C20H16Cl3NO3 详情 详情
(IX) 20392 methyl 3-(bromomethyl)benzoate 1129-28-8 C9H9BrO2 详情 详情
(X) 43336 methyl 3-[(diethoxyphosphoryl)methyl]benzoate C13H19O5P 详情 详情
(XI) 43337 methyl 3-[(E)-2-(2-chloro-4-[[3-(2,6-dichlorophenyl)-5-isopropyl-4-isoxazolyl]methoxy]phenyl)ethenyl]benzoate C29H24Cl3NO4 详情 详情
Extended Information