2-(hydroxydimethylsilyl)-5-bromo-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester

• 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: 2-(hydroxydimethylsilyl)-5-bromo-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester
• 英文别名: N-Boc-dimethyl[5-bromo-2-indolyl]silanol；Tert-butyl 5-bromo-2-[hydroxy(dimethyl)silyl]indole-1-carboxylate
• 化学式: C₁₅H₂₀BrNO₃Si
• 分子量: 370.318
• InChiKey: PEGWWYBQAMSUOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二氯二甲基硅烷 、 N-叔丁氧羰基-5-溴吲哚 在 lithium diisopropyl amide 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 18.5h， 以76%的产率得到2-(hydroxydimethylsilyl)-5-bromo-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates

  摘要：

  The preparation of pi-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.

  DOI：

  10.1021/jo7023784

文献信息

• Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates
  作者：Scott E. Denmark、John D. Baird、Christopher S. Regens

  DOI：10.1021/jo7023784

  日期：2008.2.1

  The preparation of pi-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.