methyl 4-bromo-1-ethyl-1H-pyrrole-2-carboxylate | 1311628-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-bromo-1-ethyl-1H-pyrrole-2-carboxylate
• 英文别名: methyl 4-bromo-1-ethylpyrrole-2-carboxylate
• CAS: 1311628-39-3
• 化学式: C₈H₁₀BrNO₂
• 分子量: 232.077
• InChiKey: KSTXOCIEUQYFAF-UHFFFAOYSA-N

物化性质

• 沸点：
  277.2±20.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-bromo-1-ethyl-1H-pyrrole-2-carboxylate 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到methyl 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  [EN] PHENYL DERIVATIVES AS PGE2 RECEPTOR MODULATORS
  [FR] DÉRIVÉS DE PHÉNYLE UTILISÉS EN TANT QUE MODULATEURS DES RÉCEPTEURS DES PGE2

  摘要：

  本发明涉及公式（I）的苯基衍生物 公式（I）其中（R1）n，R3，R4 a，R4b，R5b和Ar1如描述中所述，并且它们在通过调节免疫反应治疗癌症中的用途包括在肿瘤中重新激活免疫系统。该发明还涉及公式（III）的新苯并呋喃和苯并噻吩衍生物及其作为药物的用途，它们的制备，其药学上可接受的盐，以及它们作为药物的用途，含有公式（I）中一个或多个化合物的药物组合物，特别是它们作为前列腺素2受体EP2和/或EP4的调节剂的用途。

  公开号：

  WO2018210994A1
• 作为产物：
  描述：

  甲基1-乙基-1H-吡咯-2-羧酸酯 在 Ascophyllum nodosum vanadate(V)-dependent bromoperoxidase I 、 双氧水 、 sodium bromide 作用下， 以 水 、 叔丁醇 为溶剂， 反应 72.0h， 生成 methyl 4-bromo-1-ethyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Parameters for bromination of pyrroles in bromoperoxidase-catalyzed oxidations

  摘要：

  Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 degrees C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 mu mol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4-ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2-carboxamide (from Acanthella carteri). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.010

文献信息

• [EN] PYRIMIDINE DERIVATIVES AS PGE2 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE PYRIMIDINE UTILISÉS EN TANT QUE MODULATEURS DES RÉCEPTEURS DES PGE2
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2018210988A1

  公开（公告）日：2018-11-22

  The present invention relates to pyrimidine derivatives of formula (I) wherein (R1)n, R3, R4a, R4b, R5a, R5b and Ar1 are as described in the description and their use in the treatment of cancer by modulating an immune response comprising a reactivation of the immune system in the tumor. The invention further relates to novel benzofurane and benzothiophene derivatives of formula (II) and their use as pharmaceuticals, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as modulators of the prostaglandin 2 receptors EP2 and/or EP4.

  本发明涉及式(I)的嘧啶衍生物，其中(R1)n，R3，R4a，R4b，R5a，R5b和Ar1如描述中所述，以及它们通过调节免疫反应，包括肿瘤中免疫系统的再激活，用于治疗癌症。本发明进一步涉及新颖的苯并呋喃和苯并噻吩衍生物式(II)，及其作为药物的使用，其制备，药用可接受的盐，及其作为药物的使用，以及包含式(I)中一个或多个化合物的药物组合物，尤其是它们作为前列腺素2受体EP2和/或EP4的调节剂的使用。
• [EN] BENZOFURANE AND BENZOTHIOPHENE DERIVATIVES AS PGE2 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE BENZOFURANE ET DE BENZOTHIOPHÈNE UTILISÉS EN TANT QUE MODULATEURS DU RÉCEPTEUR PGE2
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2018210987A1

  公开（公告）日：2018-11-22

  The present invention relates to benzofurane and benzothiophene derivatives of formula (I) Formula (I) wherein (R1)n, R2, R3, R4a, R4b, R5a, R5b and Ar1 are as described in the description and their use in the treatment of cancer by modulating an immune response comprising a reactivation of the immune system in the tumor. The invention further relates to novel benzofurane and benzothiophene derivatives of formula (II) and their use as pharmaceuticals, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as modulators of the prostaglandin 2 receptors EP2 and/or EP4.

  本发明涉及公式(I)的苯并呋喃和苯并噻吩衍生物，其中(R1)n，R2，R3，R4a，R4b，R5a，R5b和Ar1如描述中所述，并且它们在通过调节免疫应答包括在肿瘤中重新激活免疫系统的治疗中的用途。该发明还涉及公式(II)的新型苯并呋喃和苯并噻吩衍生物及其作为药物的用途，其制备，其药学上可接受的盐，以及其作为药物的用途，含有一个或多个公式(I)化合物的药物组合物，特别是它们作为前列腺素2受体EP2和/或EP4的调节剂的用途。
• Benzofurane and benzothiophene derivatives as PGE2 receptor modulators
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：US11325899B2

  公开（公告）日：2022-05-10

  The present invention relates to benzofurane and benzothiophene derivatives of formula (I) wherein (R1)n, R2, R3, R4a, R4b, R5a, R5b and Ar1 are as described in the description and their use in the treatment of cancer by modulating an immune response comprising a reactivation of the immune system in the tumor. The invention further relates to novel benzofurane and benzothiophene derivatives of formula (II) and their use as pharmaceuticals, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as modulators of the prostaglandin 2 receptors EP2 and/or EP4.

  本发明涉及式 (I) 的苯并呋喃和苯并噻吩衍生物 其中(R1)n、R2、R3、R4a、R4b、R5a、R5b 和 Ar1 如说明书所述，以及它们通过调节免疫反应（包括重新激活肿瘤中的免疫系统）治疗癌症的用途。本发明进一步涉及式(II)的新型苯并呋喃和苯并噻吩衍生物及其作为药物的用途、它们的制备、它们的药学上可接受的盐及其作为药物的用途、含有一种或多种式(I)化合物的药物组合物，特别是它们作为前列腺素2受体EP2和/或EP4的调节剂的用途。
• PHENYL DERIVATIVES AS PGE2 RECEPTOR MODULATORS
  申请人：Idorsia Pharmaceuticals Ltd

  公开号：EP3625222A1

  公开（公告）日：2020-03-25
• BENZOFURANE AND BENZOTHIOPHENE DERIVATIVES AS PGE2 RECEPTOR MODULATORS
  申请人：Idorsia Pharmaceuticals Ltd

  公开号：EP3625227A1

  公开（公告）日：2020-03-25