5-溴-吡咯并[2,3-b]吡啶-1-羧酸叔丁酯 | 928653-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 5-溴-吡咯并[2,3-b]吡啶-1-羧酸叔丁酯
• 英文名称: tert-butyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate
• 英文别名: tert-butyl 5-bromopyrrolo[2,3-b]pyridine-1-carboxylate
• CAS: 928653-80-9
• 化学式: C₁₂H₁₃BrN₂O₂
• 分子量: 297.151
• InChiKey: IEJVSMXKNBLMND-UHFFFAOYSA-N

物化性质

• 沸点：
  361.8±45.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H302
• 危险性防范说明：
  P264,P270,P301+P312,P330,P501

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-5-Bromopyrrolo[2,3-b]pyridine
Synonyms: 5-Bromo-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 1-BOC-5-Bromopyrrolo[2,3-b]pyridine
CAS number: 928653-80-9

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C12H13BrN2O2
Molecular weight: 297.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-溴-吡咯并[2,3-b]吡啶-1-羧酸叔丁酯 在 copper(l) iodide 、 N,N'-二甲基乙二胺 作用下， 以 水 为溶剂， 反应 19.0h， 以66.2%的产率得到5-羟基-7-氮杂吲哚
  参考文献：
  名称：

  一种5-羟基-7-氮杂吲哚的制备方法

  摘要：

  本发明公开了一种5‑羟基‑7‑氮杂吲哚的制备方法，该中间体的结构对应于式Ⅲ，该方法包括使用式Ⅰ的化合物5‑溴‑7氮杂吲哚作为原料，经氮保护、羟基化并直接去保护共2步反应，最终得到式Ⅲ的5‑羟基‑7氮杂吲哚。本发明中合成方法原料便宜易得，成本低廉；并且反应条件温和，收率较高，适合工业化放大生产。

  公开号：

  CN107434807A
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 5-溴-7-氮杂吲哚 在 4-二甲氨基吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 生成 5-溴-吡咯并[2,3-b]吡啶-1-羧酸叔丁酯
  参考文献：
  名称：

  三唑基的快速制备取代的NH杂环激酶抑制剂通过一锅Sonogashira偶联-TMS-去保护- CuAAC序列†往最‡

  摘要：

  一锅三组分Sonogashira偶联-TMS-去保护-铜铝酸钙 （“点击”）序列是快速合成三聚氰胺的关键反应 三唑基 替代的 ñ -Boc 受保护的NH杂环，例如 吲哚， 吲唑，4-，5-，6-和7-氮杂吲哚， 4,7-二氮杂吲哚，7-脱氮嘌呤， 吡咯， 吡唑， 和 咪唑。随后，容易除去保护基，得到相应的保护基。三唑基这些极其重要的NH杂环的衍生物。所有化合物均已在各种激酶测定法中进行了测试。已显示几种化合物8f，8h，8k和8l抑制激酶PDK1，是具有高度肿瘤相关性的目标，因此它们很有希望 带领开发更具活性的衍生物的结构。化合物8f与配合物的X射线结构分析。PDK1 已经揭示了该分子在激酶中的详细结合模式。

  DOI：

  10.1039/c1ob05586k

文献信息

• Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis
  作者：Tomer M. Faraggi、Caroline Rouget-Virbel、Juan A. Rincón、Mario Barberis、Carlos Mateos、Susana García-Cerrada、Javier Agejas、Oscar de Frutos、David W. C. MacMillan

  DOI：10.1021/acs.oprd.1c00208

  日期：2021.8.20

  wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds

  我们在本文中描述了将丝氨酸转化为多种光学纯非天然氨基酸的两步过程。该方法利用溴代烷基中间体和多种芳基卤化物之间的光催化交叉亲电偶联来生产苯丙氨酸、色氨酸和组氨酸的人工类似物。该反应具有广泛的功能，可用于通过流动技术可扩展地合成有价值的药物支架。
• 氮杂吲哚衍生物髓细胞增殖抑制剂及其制备方法与在制药中的应用
  申请人：复旦大学

  公开号：CN113214247A

  公开（公告）日：2021-08-06

  本发明提供式I所示的氮杂吲哚衍生物髓细胞增殖抑制剂，其中R1,R2,R33均具有本发明说明书中所限定的含义。式I化合物可显著抑制以MOLM‑16，HL‑60，MV‑4‑11为代表的髓细胞增殖及其相关病症。本发明提供的式I或其盐或相关药物组合，具有优异的体内外抑制活性、良好的成药性，且生物利用度高，对脏器无明显损伤。因此，式I或其盐及相关药物组合具有巨大的临床应用前景。
• The application of nitrogen heterocycles in mitochondrial-targeting fluorescent markers with neutral skeletons
  作者：Yue Wang、Bing Xu、Ru Sun、Yu-Jie Xu、Jian-Feng Ge

  DOI：10.1039/d0tb01377c

  日期：——

  1H-indazole and 1H-pyrrolo[2,3-b]pyridine) as targeting groups were designed and prepared in order to screen out structural units for targeting mitochondria. Several classical fluorophores (coumarin, 1,8-naphthalimide and Nile Red) were connected with these heterocycles via Suzuki coupling reactions. The derivatives of coumarin (dyes 1a and 2a–c) and 1,8-naphthalimide (dyes 3a–c) fluoresced in the blue-green

  设计并制备了四种不同的含氮杂环的中性荧光标记物（喹喔啉，1 H-吡唑并[3,4- b ]吡啶，1 H-吲唑和1 H-吡咯并[2,3- b ]吡啶）作为靶向基团。为了筛选出针对线粒体的结构单元。几种经典的荧光团（香豆素，1,8-萘二甲酰亚胺和尼罗红）通过Suzuki偶联反应与这些杂环连接。香豆素（染料1a和2a–c）和1,8-萘二甲酰亚胺（染料3a–c）的衍生物在蓝绿色区域发出荧光，而尼罗红衍生物（染料1b和2d）则发荧光。4a–c）在红光区域发出荧光。新染料保留了经典荧光团的光学性质，例如发射性质和光稳定性。它们均显示出低细胞毒性。在L929正常细胞和HeLa癌细胞中进行的共聚焦荧光实验表明，染料1a–b靶向线粒体和脂质液滴的双重位点。此外，染料2a–c，3a–c和4a–c靶向线粒体。同时，仅有少数具有中性骨架的线粒体靶向标记。此外，还发现带有NH键的氮杂环可以提高部分中性荧光团的线粒体靶向能力。
• 基于含氮杂环的中性线粒体荧光标记物及其 制备方法与应用
  申请人：苏州大学

  公开号：CN111440143B

  公开（公告）日：2021-04-27

  本发明公开了基于含氮杂环的中性线粒体荧光标记物及其制备方法与应用，本发明首次公开的中性荧光团为含有N‑H键的杂环，靶向线粒体解决了现有中性结构的荧光染料细胞器靶向能力是随机的且不确定的问题，也避免中性荧光团是细胞中脂滴的商业标记物的问题，本发明改善荧光团良好的光学性能的同时，通过对其结构创造性的修饰来调控原荧光团的细胞器靶向能力，而且标记物改善荧光团的生物学性能，含氮杂环砌块廉价易得，有利于控制新染料的成本，具有重大的科学意义和商业价值。
• PYRROLOPYRIDINYLPYRIMIDIN-2-YLAMINE DERIVATIVES
  申请人：Wucherer-Plietker Margarita

  公开号：US20120270871A1

  公开（公告）日：2012-10-25

  Pyrrolopyridinylpyrimidin-2-ylamine derivatives of the formula (I), in which R 1 -R 6 and R 1 have the meanings indicated in claim 1 , are inhibitors of cell proliferation/cell vitality and can be employed for the treatment of tumours.

  公式（I）中的吡咯吡啶基嘧啶-2-胺衍生物，其中R1-R6和R1具有权利要求书中指示的含义，是细胞增殖/细胞活力的抑制剂，可用于肿瘤的治疗。