1-(3-碘-1H-吡咯并[2,3-b]吡啶-5-基)乙酮 | 1015609-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 1-(3-碘-1H-吡咯并[2,3-b]吡啶-5-基)乙酮
• 英文名称: 1-(3-iodo-1H-pyrrolo-[2,3-b]pyridin-5-yl)ethan-1-one
• 英文别名: 1-(3-Iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)ethanone
• CAS: 1015609-03-6
• 化学式: C₉H₇IN₂O
• mdl: MFCD09763668
• 分子量: 286.072
• InChiKey: SGQVDDRXKXQBMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-碘-1H-吡咯并[2,3-b]吡啶-5-基)乙酮 、 对甲苯磺酰氯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.0h， 以60%的产率得到1-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethan-1-one
  参考文献：
  名称：

  Synthesis of Differentially Protected Azatryptophan Analogs via Pd₂(dba)₃/XPhos Catalyzed Negishi Coupling of N-Ts Azaindole Halides with Zinc Derivative from Fmoc-Protected tert-Butyl (R)-2-Amino-3-iodopropanoate

  摘要：

  Unnatural amino acids play an important role in peptide based drug discovery. Herein, we report a class of differentially protected azatryptophan derivatives synthesized from N-tosyl-3-haloazaindoles 1 and Fmoc-protected tert-butyl iodoalanine 2 via a Negishi coupling. Through ligand screening, Pd-2(dba)(3)/XPhos was found to be a superior catalyst for the coupling of 1 with the zinc derivative of 2 to give tert-butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate derivatives 3 in 69-91% isolated yields. In addition, we have demonstrated that the protecting groups, namely, Ts, Fmoc, and Bu-t, can be easily removed selectively.

  DOI：

  10.1021/acs.joc.0c00973

文献信息

• Synthesis of Differentially Protected Azatryptophan Analogs via Pd₂(dba)₃/XPhos Catalyzed Negishi Coupling of <i>N</i>-Ts Azaindole Halides with Zinc Derivative from Fmoc-Protected <i>tert</i>-Butyl (<i>R</i>)-2-Amino-3-iodopropanoate
  作者：Roshan Y Nimje、Devaiah Vytla、Prakasam Kuppusamy、Rajeswari Velayuthaperumal、Lokesh Babu Jarugu、China Anki Reddy、Nanjundaswamy Kanikahalli Chikkananjaiah、Richard A. Rampulla、Cullen L. Cavallaro、Jianqing Li、Arvind Mathur、Anuradha Gupta、Amrita Roy

  DOI：10.1021/acs.joc.0c00973

  日期：2020.9.4

  Unnatural amino acids play an important role in peptide based drug discovery. Herein, we report a class of differentially protected azatryptophan derivatives synthesized from N-tosyl-3-haloazaindoles 1 and Fmoc-protected tert-butyl iodoalanine 2 via a Negishi coupling. Through ligand screening, Pd-2(dba)(3)/XPhos was found to be a superior catalyst for the coupling of 1 with the zinc derivative of 2 to give tert-butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate derivatives 3 in 69-91% isolated yields. In addition, we have demonstrated that the protecting groups, namely, Ts, Fmoc, and Bu-t, can be easily removed selectively.