1-(4-bromophenyl)-4-chloro-1H-imidazole | 1605347-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-bromophenyl)-4-chloro-1H-imidazole
• 英文别名: 1-(4-Bromophenyl)-4-chloroimidazole；1-(4-bromophenyl)-4-chloroimidazole
• CAS: 1605347-54-3
• 化学式: C₉H₆BrClN₂
• 分子量: 257.517
• InChiKey: ZYCFNGXLTQILIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(4-溴苯基)咪唑 在 2-chloro-1,3-bis(methoxycarbonyl)guanidine 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以43%的产率得到1-(4-bromophenyl)-4-chloro-1H-imidazole
  参考文献：
  名称：

  Palau’chlor: A Practical and Reactive Chlorinating Reagent

  摘要：

  Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palau'chlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated pi-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.

  DOI：

  10.1021/ja5031744

文献信息

• Bicyclic heteroaryl derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US10647721B2

  公开（公告）日：2020-05-12

  The present invention relates to a compound of formula (I), wherein R1 is hydrogen, lower alkyl, lower alkyl substituted by halogen, halogen, lower alkoxy or lower alkoxy substituted by halogen; and R1 may be different if n is 2 or 3; R2 is hydrogen, lower alkyl, lower alkyl substituted by halogen, halogen, CN, lower alkoxy or lower alkoxy substituted by halogen; X is CH or N; m is 1, 2 or 3; -( )m is —(CH2)m—; n is 1, 2 or 3; Ar is a five membered heteroaryl group, selected from formula (A), (B), (C), (D), (E) or (F), wherein R3 is hydrogen, methyl or chloro; R4 is hydrogen or methyl; R5 is F, Cl, CHF2 or CF3; or to pharmaceutically active acid addition salts thereof. The compounds may be used for the treatment of Alzheimer's disease, cerebral amyloid angiopathy, hereditary cerebral hemorrhage with amyloidosis, Dutch-type (HCHWA-D), multi-infarct dementia, dementia pugilistica or Down syndrome.

  本发明涉及式(I)化合物，其中R1是氢、低级烷基、被卤素取代的低级烷基、卤素、低级烷氧基或被卤素取代的低级烷氧基；如果n是2或3，R1可以不同；R2是氢、低级烷基、被卤素取代的低级烷基、卤素、CN、低级烷氧基或被卤素取代的低级烷氧基；X是CH或N；m是1、2或3；-( )m是-(CH2)m-；n是1、2或3；Ar是选自式(A)、(B)、(C)、(D)、(E)或(F)的五元杂芳基，其中R3是氢、甲基或氯；R4是氢或甲基；R5是F、Cl、CHF2或CF3；或其药用活性酸加成盐。这些化合物可用于治疗阿尔茨海默病、脑淀粉样血管病、遗传性脑出血伴淀粉样变性、荷兰型（HCHWA-D）、多梗塞性痴呆、帕金森痴呆或唐氏综合征。
• BICYCLIC HETEROARYL DERIVATIVES
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3523304B1

  公开（公告）日：2021-01-27