• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】19789

【品名】bromo[4-(methylsulfanyl)benzyl]magnesium

【CA登记号】

【 分 子 式 】C8H9BrMgS

【 分 子 量 】241.43446

【元素组成】C 39.8% H 3.76% Br 33.1% Mg 10.07% S 13.28%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

The Grignard condensation of N-methoxy-N-methylbenzamide (I) with 4-(methylsulfanyl)benzylmagnesium bromide (II) in THF gives the expected ketone (III), which is brominated with Br2 in CCl4 yielding the alpha-bromoketone (IV). The oxidation of the thioether group of (IV) with oxone (potassium peroxymonosulfate) in dichloromethane/methanol/tert-butanol/water affords the corresponding sulfone (V) (1), which is finally cyclocondesed with thiazol-2-amine (VI) in refluxing ethanol or isopentanol.

1 Gauthier, J.Y.; Lau, C.K.; Leblanc, Y.; Li, C.-S.; Roy, P.; Therien, M.; Wang, Z. (Merck Frosst Canada Inc.); Aryl substd. 5,5 fused aromatic nitrogen cpds. as anti-inflammatory agents. EP 0802917; JP 1999501902; US 5552422; WO 9621667 .
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) 19789 bromo[4-(methylsulfanyl)benzyl]magnesium C8H9BrMgS 详情 详情
(II) 19788 N-methoxy-N-methylbenzamide C9H11NO2 详情 详情
(III) 19790 2-[4-(methylsulfanyl)phenyl]-1-phenyl-1-ethanone C15H14OS 详情 详情
(IV) 19791 2-bromo-2-[4-(methylsulfanyl)phenyl]-1-phenyl-1-ethanone C15H13BrOS 详情 详情
(V) 19792 2-bromo-2-[4-(methylsulfonyl)phenyl]-1-phenyl-1-ethanone C15H13BrO3S 详情 详情
(VI) 19795 2-Thiazolamine; 1,3-thiazol-2-amine; 1,3-thiazol-2-ylamine 96-50-4 C3H4N2S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

The Grignard condensation of N-methoxy-N-methylbenzamide (I) with 4-(methylsulfanyl)benzylmagnesium bromide (II) in THF gives the expected ketone (III), which is brominated with Br2 in CCl4 yielding the alpha-bromoketone (IV). The oxidation of the thioether group of (IV) with oxone (potassium peroxymonosulfate) in dichloromethane/methanol/tert-butanol/water affords the corresponding sulfone (V) (1), which is condesed with 4H-1,2,4-triazole-3-thiol (VI) in refluxing ethanol to give 2-[4-(methylsulfonyl)phenyl]-1-phenyl-2-(4H-1,2,4-triazol-3-ylsulfanyl)ethanone (VII). Finally, this compound is cyclized with polyphosphoric acid (PPA) in refluxing xylene.

1 Therien, M.; et al.; Synthesis and biological evaluation of 5, 6-diarylimidazo[2.1-b]thiazole as selective COX-2 inhibitors. Bioorg Med Chem Lett 1997, 7, 1, 47.
2 Trimble, L.A.; et al.; Characterization of the in vitro oxidative metabolites of the COX-2 selective inhibitor L-766,112. Bioorg Med Chem Lett 1997, 7, 1, 53.
3 Roy, P.; et al.; A new series of selective COX-2 inhibitors: 5, 6-Diarylthiazolo[3,2-b][1,2,4]triazoles. Bioorg Med Chem Lett 1997, 7, 1, 57.
4 Gauthier, J.Y.; Lau, C.K.; Leblanc, Y.; Li, C.-S.; Roy, P.; Therien, M.; Wang, Z. (Merck Frosst Canada Inc.); Aryl substd. 5,5 fused aromatic nitrogen cpds. as anti-inflammatory agents. EP 0802917; JP 1999501902; US 5552422; WO 9621667 .
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) 19788 N-methoxy-N-methylbenzamide C9H11NO2 详情 详情
(II) 19789 bromo[4-(methylsulfanyl)benzyl]magnesium C8H9BrMgS 详情 详情
(III) 19790 2-[4-(methylsulfanyl)phenyl]-1-phenyl-1-ethanone C15H14OS 详情 详情
(IV) 19791 2-bromo-2-[4-(methylsulfanyl)phenyl]-1-phenyl-1-ethanone C15H13BrOS 详情 详情
(V) 19792 2-bromo-2-[4-(methylsulfonyl)phenyl]-1-phenyl-1-ethanone C15H13BrO3S 详情 详情
(VI) 19793 4H-1,2,4-triazol-3-ylhydrosulfide; 4H-1,2,4-triazole-3-thiol C2H3N3S 详情 详情
(VII) 19794 2-[4-(methylsulfonyl)phenyl]-1-phenyl-2-(4H-1,2,4-triazol-3-ylsulfanyl)-1-ethanone C17H15N3O3S2 详情 详情
Extended Information