2-methyl-3-carbometoxy-5-chlorofuro[3,2-b]pyridine | 289714-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: 2-methyl-3-carbometoxy-5-chlorofuro[3,2-b]pyridine
• 英文别名: Methyl 2-(5-chloro-2-methylfuro[3,2-b]pyridin-3-yl)acetate
• CAS: 289714-32-5
• 化学式: C₁₁H₁₀ClNO₃
• 分子量: 239.658
• InChiKey: VOXOKFBCBSXULP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-3-carbometoxy-5-chlorofuro[3,2-b]pyridine 在 tris(dibenzylideneacetone)dipalladium (0) 二苯甲酮亚胺 、 三甲基铝 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 5-amino-3-[2-(N,N-dimethylamino)ethyl]-2-methylfuro[3,2-b]pyridine
  参考文献：
  名称：

  A general method for the preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines

  摘要：

  The preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines via a Pd(0)-catalyzed intramolecular cyclization of methyl 4-(6-chloro-2-iodopyridin-3-yloxy)-substituted-butenoates 9a-f is described. This approach was both efficient and general, and provided the highly functionalized heterocyclic ring system in high yield. Among the several examples provided is the preparation of 3-[2-(N,N-dimethylamino)ethyl]-5-(4-fluorobenzoyl)amino-2-methylfuro[3,2-b]pyridine 4, a selective 5-HTIF receptor agonist. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02655-2
• 作为产物：
  描述：

  6-氯-3-吡啶基乙酸酯 在 palladium diacetate 四丁基氯化铵 、 碘 、 sodium formate 、 sodium carbonate 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-methyl-3-carbometoxy-5-chlorofuro[3,2-b]pyridine
  参考文献：
  名称：

  A general method for the preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines

  摘要：

  The preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines via a Pd(0)-catalyzed intramolecular cyclization of methyl 4-(6-chloro-2-iodopyridin-3-yloxy)-substituted-butenoates 9a-f is described. This approach was both efficient and general, and provided the highly functionalized heterocyclic ring system in high yield. Among the several examples provided is the preparation of 3-[2-(N,N-dimethylamino)ethyl]-5-(4-fluorobenzoyl)amino-2-methylfuro[3,2-b]pyridine 4, a selective 5-HTIF receptor agonist. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02655-2

文献信息

• A general method for the preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines
  作者：Brian M Mathes、Sandra A Filla

  DOI：10.1016/s0040-4039(02)02655-2

  日期：2003.1

  The preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines via a Pd(0)-catalyzed intramolecular cyclization of methyl 4-(6-chloro-2-iodopyridin-3-yloxy)-substituted-butenoates 9a-f is described. This approach was both efficient and general, and provided the highly functionalized heterocyclic ring system in high yield. Among the several examples provided is the preparation of 3-[2-(N,N-dimethylamino)ethyl]-5-(4-fluorobenzoyl)amino-2-methylfuro[3,2-b]pyridine 4, a selective 5-HTIF receptor agonist. (C) 2003 Elsevier Science Ltd. All rights reserved.