3-(4-fluorophenyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile | 1014692-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 3-(4-fluorophenyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile
• 英文别名: 3-(4-fluorophenyl)-4-oxo-7H-thieno[2,3-b]pyridine-5-carbonitrile
• CAS: 1014692-66-0
• 化学式: C₁₄H₇FN₂OS
• 分子量: 270.287
• InChiKey: QAPIGRVJRGLXCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-ethyl 2-(3-tert-butoxy-2-cyano-3-oxoprop-1-enylamino)-4-(4-fluorophenyl)thiophene-3-carboxylate 以 二苯醚 为溶剂， 反应 2.0h， 以87%的产率得到3-(4-fluorophenyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  A facile, scalable preparation of 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles

  摘要：

  We report a new synthesis of thieno[2,3-b]pyridine-5-carbonitriles from 2-aminothiophene-3-carboxylate esters. The key step of the synthesis is a thermally promoted elimination/decarboxylation followed by nucleophilic cyclization to give 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles. The reactions proceed in good yield and generally require no chromatographic purification. These compounds are easily transformed in two steps to 4-chloro-2-iodothieno[2,3-b]pyridine-5-carbonitriles which are key intermediates in the synthesis of various kinase inhibitors. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.107

文献信息

• Process for the preparation of 4-hydroxythieno[2,3-b]pyridine-5-carbonitriles
  申请人：Boschelli Harris Diane

  公开号：US20080076926A1

  公开（公告）日：2008-03-27

  A process for the preparation of 4-hydroxythieno[2,3-b]pyridine-5-carbonitriles, which can be useful for the preparation of protein kinase inhibitors, is provided.

  提供一种制备4-羟基噻吩[2,3-b]吡啶-5-碳腈的方法，该方法可用于制备蛋白激酶抑制剂。
• PROCESS FOR THE PREPARATION OF 4-HYDROXYTHIENO[2,3-B]PYRIDINE-5-CARBONITRILES
  申请人：Wyeth

  公开号：EP2066675A1

  公开（公告）日：2009-06-10
• [EN] PROCESS FOR THE PREPARATION OF 4-HYDROXYTHIENO[2,3-B]PYRIDINE-5-CARBONITRILES<br/>[FR] PROCÉDÉ DE PRODUCTION DE 4-HYDROXYTHIÉNO[2,3-B]PYRIDINE-5-CARBONITRILES
  申请人：WYETH CORP

  公开号：WO2008039414A1

  公开（公告）日：2008-04-03

  [EN] A process for the preparation of 4-hydroxythieno[2,3-b]pyridine-5-carbonitriles, which can be useful for the preparation of protein kinase inhibitors, is provided.
  [FR] La présente invention concerne un procédé de préparation de 4-hydroxythiéno[2,3-b]pyridine-5-carbonitriles qui peuvent être utilisés pour préparer des inhibiteurs de protéine kinase.
• A facile, scalable preparation of 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles
  作者：L. Nathan Tumey、Niala Bhagirath、Biqi Wu、Diane H. Boschelli

  DOI：10.1016/j.tetlet.2008.09.107

  日期：2008.11

  We report a new synthesis of thieno[2,3-b]pyridine-5-carbonitriles from 2-aminothiophene-3-carboxylate esters. The key step of the synthesis is a thermally promoted elimination/decarboxylation followed by nucleophilic cyclization to give 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles. The reactions proceed in good yield and generally require no chromatographic purification. These compounds are easily transformed in two steps to 4-chloro-2-iodothieno[2,3-b]pyridine-5-carbonitriles which are key intermediates in the synthesis of various kinase inhibitors. (c) 2008 Elsevier Ltd. All rights reserved.