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【结 构 式】

【分子编号】53025

【品名】2,3-Dichlorophenol

【CA登记号】576-24-9

【 分 子 式 】C6H4Cl2O

【 分 子 量 】163.00256

【元素组成】C 44.21% H 2.47% Cl 43.5% O 9.82%

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:(XI)

In a related method, electrophilic bromination of 2,3-dichlorophenol (XI) gave (XII). Heck reaction of bromide (XII) with methyl acrylate (XIII) produced the cinnamic acid derivative (XIV). Sulfonylation of the phenolic hydroxyl of (XIV) with trifluoromethanesulfonic anhydride in pyridine furnished the aryl triflate (XV). This was coupled with the silyl sulfide intermediate (II) in the presence of CsF to produce the diaryl sulfide (XVI). After methyl ester (XVI) hydrolysis, the resultant cinnamic acid (VIII) was coupled with methyl isonipecotate (XVII) to furnish amide (XVIII). The title compound was then obtained by methyl ester (XVIII) hydrolysis with LiOH, followed by treatment with methanolic NaOH.

1 Jae, H.-S.; Pei, Z.; Staeger, M.A.; Gunawardana, I.W.; Winn, M.; Freeman, J.C.; Liu, G.; Link, J.; Boyd, S.A.; Zhu, G.-D.; Von Geldern, T.W.; Xin, Z.; Lynch, J.K.; Wang, S. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory and immune-suppressive cpds.. WO 0059880 .
2 Lynch, J.K.; Link, J.; Zhu, G.-D.; Boyd, S.A.; Winn, M.; Pei, Z.; Gunawardana, I.W.; Liu, G.; Xin, Z.; Jae, H.-S.; Freeman, J.C.; Von Geldern, T.; Staeger, M.A. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory and immune-suppressive cpds.. US 6110922; WO 0039081 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 53020 1-methyl-5-[(triisopropylsilyl)sulfanyl]-1H-indole; 1-methyl-1H-indol-5-yl triisopropylsilyl sulfide n/a C18H29NSSi 详情 详情
(VIII) 53023 (E)-3-{2,3-dichloro-4-[(1-methyl-1H-indol-5-yl)sulfanyl]phenyl}-2-propenoic acid n/a C18H13Cl2NO2S 详情 详情
(XI) 53025 2,3-Dichlorophenol 576-24-9 C6H4Cl2O 详情 详情
(XII) 53026 4-bromo-2,3-dichlorophenol n/a C6H3BrCl2O 详情 详情
(XIII) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(XIV) 53027 methyl (E)-3-(2,3-dichloro-4-hydroxyphenyl)-2-propenoate n/a C10H8Cl2O3 详情 详情
(XV) 53028 methyl (E)-3-(2,3-dichloro-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)-2-propenoate n/a C11H7Cl2F3O5S 详情 详情
(XVI) 53029 methyl (E)-3-{2,3-dichloro-4-[(1-methyl-1H-indol-5-yl)sulfanyl]phenyl}-2-propenoate n/a C19H15Cl2NO2S 详情 详情
(XVII) 38418 methyl 4-piperidinecarboxylate; Isonipecotic acid methyl ester; 4-piperidinecarboxylic acid methyl ester 2971-79-1 C7H13NO2 详情 详情
(XVIII) 53030 methyl 1-((E)-3-{2,3-dichloro-4-[(1-methyl-1H-indol-5-yl)sulfanyl]phenyl}-2-propenoyl)-4-piperidinecarboxylate n/a C25H24Cl2N2O3S 详情 详情
Extended Information