N,N-diethyl-1-(methoxymethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-sulfonamide | 1312206-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N,N-diethyl-1-(methoxymethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-sulfonamide
• 英文别名: N,N-diethyl-1-(methoxymethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-3-sulfonamide
• CAS: 1312206-38-4
• 化学式: C₂₀H₃₁BN₂O₅S
• 分子量: 422.354
• InChiKey: XFKXUJJZBZUROA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-溴苯甲醚 、 N,N-diethyl-1-(methoxymethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-sulfonamide 在 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 12.0h， 以74%的产率得到N,N-diethyl-1-(methoxymethyl)-2-(4-methoxyphenyl)-1H-indole-3-sulfonamide
  参考文献：
  名称：

  Directed ortho-Metalation–Cross-Coupling Strategies. One-Pot Suzuki Reaction to Biaryl and Heterobiaryl Sulfonamides

  摘要：

  A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (DoM) and either MeOBPin or i-PrOBpin electrophile quench, 3 -> 4, is described. A one-pot metalation-Suzuki cross-coupling procedure for the synthesis of biaryis and heteroblaryls, 3 -> 5, and a complementary DoM-Ir-catalyzed boronation sequence (Scheme 6) are delineated.

  DOI：

  10.1021/ol201175g
• 作为产物：
  描述：

  1H-吲哚-3-磺酰氯 在 咪唑 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 N,N-diethyl-1-(methoxymethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-sulfonamide
  参考文献：
  名称：

  Directed ortho-Metalation–Cross-Coupling Strategies. One-Pot Suzuki Reaction to Biaryl and Heterobiaryl Sulfonamides

  摘要：

  A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (DoM) and either MeOBPin or i-PrOBpin electrophile quench, 3 -> 4, is described. A one-pot metalation-Suzuki cross-coupling procedure for the synthesis of biaryis and heteroblaryls, 3 -> 5, and a complementary DoM-Ir-catalyzed boronation sequence (Scheme 6) are delineated.

  DOI：

  10.1021/ol201175g

文献信息

• Directed <i>ortho</i>-Metalation–Cross-Coupling Strategies. One-Pot Suzuki Reaction to Biaryl and Heterobiaryl Sulfonamides
  作者：Cédric Schneider、Ellen Broda、Victor Snieckus

  DOI：10.1021/ol201175g

  日期：2011.7.15

  A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (DoM) and either MeOBPin or i-PrOBpin electrophile quench, 3 -> 4, is described. A one-pot metalation-Suzuki cross-coupling procedure for the synthesis of biaryis and heteroblaryls, 3 -> 5, and a complementary DoM-Ir-catalyzed boronation sequence (Scheme 6) are delineated.