5-bromo-3-methyl-2-phenylpyridine | 1469759-14-5

• 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: 5-bromo-3-methyl-2-phenylpyridine
• 英文别名: 3-bromo-5-methyl-6-phenylpyridine；5-Bromo-3-methyl-2-phenylpyridine
• CAS: 1469759-14-5
• 化学式: C₁₂H₁₀BrN
• 分子量: 248.122
• InChiKey: AVQMLSHZHKAMBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2,5-二溴-3-甲基吡啶 、 苯硼酸 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 以88%的产率得到5-bromo-3-methyl-2-phenylpyridine
  参考文献：
  名称：

  Palladium-catalyzed highly regioselective 2-arylation of 2,x-dibromopyridines and its application in the efficient synthesis of a 17β-HSD1 inhibitor

  摘要：

  2,3- and 2,5-Dibromopyridines reacted with arylboronic acids, catalyzed by Pd(OAc)(2)/PPh3 in the presence of K2CO3 in CH3CN/MeOH (2:1) at 50 degrees C for 24 h, to afford 2-aiylpyridines in good to high yields, while 2,4-dibromopyridine reacted with arylboronic acid pinacol esters, catalyzed by Pd(OAc)(2)/PPh3 in the presence of KOH in CH3CN at 70 degrees C for 24 h, to afford 2-arylpyridines in good to high yields. To expand this methodology, a 170-HSD1 inhibitor was synthesized in good yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.065

文献信息

• Substituted pyridines from isoxazoles: scope and mechanism
  作者：Seokjoo Lee、Rashmi Jena、Aaron L. Odom

  DOI：10.1039/d2ob00779g

  日期：——

  Treatment of isoxazoles with enamines leads to an inverse electron-demand hetero-Diels–Alder reaction that produces substituted pyridines in the presence of TiCl4(THF)2 and titanium powder. The reaction is highly regioselective with only a single isomer of the product observed by GC/MS and tolerant of many common functional groups. The transformation was examined computationally, and it was found that

  用烯胺处理异恶唑会导致在 TiCl 4 (THF) 2和钛粉存在下产生取代的吡啶的逆电子需求杂狄尔斯-阿尔德反应。该反应具有高度区域选择性，通过 GC/MS 仅观察到产物的单一异构体，并且耐受许多常见的官能团。对转化进行了计算检查，发现 TiCl 4（或类似的路易斯酸）可能起到催化反应的作用。在最初的 [4 + 2]-环加成之后，恶氮杂-[2.2.1]-二环在胺损失之前可能会开环以产生N-氧化物。然后用TiCl 4和钛粉还原后得到吡啶。
• PYRROLIDINYL UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS
  申请人：ARRAY BIOPHARMA INC.

  公开号：US20160297796A1

  公开（公告）日：2016-10-13

  Compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts, or solvates or prodrugs thereof, where R 1 , R 2 , R a , R b , R c , R d , X, Ring B, and Ring C are as defined herein, and wherein Ring B moiety and the NH—C(═X)—NH moiety are in the trans configuration, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis and pelvic pain syndrome.
• US9828360B2
  申请人：——

  公开号：US9828360B2

  公开（公告）日：2017-11-28