4-(benzothiophen-5-yl)-7-bromo-2-methyl-1,2-dihydroisoquinolin-3(4H)-one | 1357254-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-(benzothiophen-5-yl)-7-bromo-2-methyl-1,2-dihydroisoquinolin-3(4H)-one
• 英文别名: 4-(1-Benzothiophen-5-yl)-7-bromo-2-methyl-1,4-dihydroisoquinolin-3-one；4-(1-benzothiophen-5-yl)-7-bromo-2-methyl-1,4-dihydroisoquinolin-3-one
• CAS: 1357254-34-2
• 化学式: C₁₈H₁₄BrNOS
• 分子量: 372.285
• InChiKey: ZNSDQULGZOJERN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(benzothiophen-5-yl)-7-bromo-2-methyl-1,2-dihydroisoquinolin-3(4H)-one 在 dimethyl sulfide borane 、 potassium tert-butylate 、 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 4.17h， 生成 4-(4-(benzothiophen-5-yl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)morpholine maleate
  参考文献：
  名称：

  Initial Process Development and Scale-Up of the Synthesis of a Triple Reuptake Inhibitor ALB 109780

  摘要：

  Early process development toward a triple reuptake inhibitor is described. Three different routes were evaluated; one of them was optimized and scaled up to generate 470 g of API as this route minimized the formation of undesired side products. The selected route featured Eaton's reagent-mediated cyclization of a phenyl acetamide, copper-mediated Buchwald Hartwig coupling to install a morpholine moiety, and palladium-catalyzed alpha-arylation of a dihydroisoquinolinone to construct the core structure.

  DOI：

  10.1021/op3000064
• 作为产物：
  描述：

  2-(4-溴苯基)-N-甲基乙酰胺 在 磷酸 、 palladium diacetate 、 sodium t-butanolate 、 2,8,9-三异丁基-2,5,8,9-四氮杂-1-磷酸双向环[3.3.3]十一烷 作用下， 以 甲苯 为溶剂， 生成 4-(benzothiophen-5-yl)-7-bromo-2-methyl-1,2-dihydroisoquinolin-3(4H)-one
  参考文献：
  名称：

  Initial Process Development and Scale-Up of the Synthesis of a Triple Reuptake Inhibitor ALB 109780

  摘要：

  Early process development toward a triple reuptake inhibitor is described. Three different routes were evaluated; one of them was optimized and scaled up to generate 470 g of API as this route minimized the formation of undesired side products. The selected route featured Eaton's reagent-mediated cyclization of a phenyl acetamide, copper-mediated Buchwald Hartwig coupling to install a morpholine moiety, and palladium-catalyzed alpha-arylation of a dihydroisoquinolinone to construct the core structure.

  DOI：

  10.1021/op3000064

文献信息

• Initial Process Development and Scale-Up of the Synthesis of a Triple Reuptake Inhibitor ALB 109780
  作者：Qiang Yang、Luckner G. Ulysse、Mark D. McLaws、Daniel K. Keefe、Brian P. Haney、Congxiang Zha、Peter R. Guzzo、Shuang Liu

  DOI：10.1021/op3000064

  日期：2012.3.16

  Early process development toward a triple reuptake inhibitor is described. Three different routes were evaluated; one of them was optimized and scaled up to generate 470 g of API as this route minimized the formation of undesired side products. The selected route featured Eaton's reagent-mediated cyclization of a phenyl acetamide, copper-mediated Buchwald Hartwig coupling to install a morpholine moiety, and palladium-catalyzed alpha-arylation of a dihydroisoquinolinone to construct the core structure.