Tert-butyl 2-[6-[(2-methylpropan-2-yl)oxycarbonyl]pyridin-3-yl]-1,3-thiazole-4-carboxylate | 1037747-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Tert-butyl 2-[6-[(2-methylpropan-2-yl)oxycarbonyl]pyridin-3-yl]-1,3-thiazole-4-carboxylate
• CAS: 1037747-33-3
• 化学式: C₁₈H₂₂N₂O₄S
• 分子量: 362.45
• InChiKey: NGGAADRVVLOCEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-[6-[(2-methylpropan-2-yl)oxycarbonyl]pyridin-3-yl]-1,3-thiazole-4-carboxylate 在 过氧化脲素 、 三氟乙酸酐 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以92%的产率得到
  参考文献：
  名称：

  Direct C-2 Arylation of Alkyl 4-Thiazolecarboxylates: New Insights in Synthesis of Heterocyclic Core of Thiopeptide Antibiotics

  摘要：

  The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.

  DOI：

  10.1021/ol801035c
• 作为产物：
  描述：

  5-溴吡啶甲酸叔丁酯 、 tert-butyl thiazole-4-carboxylate 在 palladium diacetate 、 caesium carbonate 、 2-(二环己基膦基)联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以70%的产率得到Tert-butyl 2-[6-[(2-methylpropan-2-yl)oxycarbonyl]pyridin-3-yl]-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  Direct C-2 Arylation of Alkyl 4-Thiazolecarboxylates: New Insights in Synthesis of Heterocyclic Core of Thiopeptide Antibiotics

  摘要：

  The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.

  DOI：

  10.1021/ol801035c

文献信息

• Direct C-2 Arylation of Alkyl 4-Thiazolecarboxylates: New Insights in Synthesis of Heterocyclic Core of Thiopeptide Antibiotics
  作者：Thibaut Martin、Cécile Verrier、Christophe Hoarau、Francis Marsais

  DOI：10.1021/ol801035c

  日期：2008.7.3

  The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.