4-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)but-3-yn-1-ol | 1173657-02-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)but-3-yn-1-ol
• 英文别名: 3-Butyn-1-ol, 4-[4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-；4-[1-(benzenesulfonyl)-4-chloropyrrolo[2,3-b]pyridin-2-yl]but-3-yn-1-ol
• CAS: 1173657-02-7
• 化学式: C₁₇H₁₃ClN₂O₃S
• 分子量: 360.821
• InChiKey: IHLVGYHKCOYSKP-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  595.2±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)but-3-yn-1-ol 、 苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 以65%的产率得到3-Butyn-1-ol, 4-[4-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-
  参考文献：
  名称：

  A highly effective synthesis of 2-alkynyl-7-azaindoles: Pd/C-mediated alkynylation of heteroaryl halides in water

  摘要：

  The reaction of 4-chloro-2-iodo-7-azaindole with terminal alkynes was investigated using 10% Pd/C-PPh3-Cul as a catalyst system in water. This study afforded a new, mild and selective process for the preparation of 2-alkynyl-4-chloro-7-azaindole in good yields via C-C bond forming reaction. The resulting chloro, derivative can be functionalized further via another Pd-mediated C-C bond forming reaction with arylboronic acid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.054
• 作为产物：
  描述：

  1-苯磺酰基-4-氯-2-碘-7-氮杂吲哚 、 3-丁炔-1-醇 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 水 为溶剂， 以85%的产率得到4-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)but-3-yn-1-ol
  参考文献：
  名称：

  A highly effective synthesis of 2-alkynyl-7-azaindoles: Pd/C-mediated alkynylation of heteroaryl halides in water

  摘要：

  The reaction of 4-chloro-2-iodo-7-azaindole with terminal alkynes was investigated using 10% Pd/C-PPh3-Cul as a catalyst system in water. This study afforded a new, mild and selective process for the preparation of 2-alkynyl-4-chloro-7-azaindole in good yields via C-C bond forming reaction. The resulting chloro, derivative can be functionalized further via another Pd-mediated C-C bond forming reaction with arylboronic acid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.054

文献信息

• A highly effective synthesis of 2-alkynyl-7-azaindoles: Pd/C-mediated alkynylation of heteroaryl halides in water
  作者：Mohosin Layek、Vikas Gajare、Dipak Kalita、Aminul Islam、K. Mukkanti、Manojit Pal

  DOI：10.1016/j.tet.2009.04.054

  日期：2009.6

  The reaction of 4-chloro-2-iodo-7-azaindole with terminal alkynes was investigated using 10% Pd/C-PPh3-Cul as a catalyst system in water. This study afforded a new, mild and selective process for the preparation of 2-alkynyl-4-chloro-7-azaindole in good yields via C-C bond forming reaction. The resulting chloro, derivative can be functionalized further via another Pd-mediated C-C bond forming reaction with arylboronic acid. (C) 2009 Elsevier Ltd. All rights reserved.