5-溴吲哚-3-羧酸甲酯 | 773873-77-1

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-溴吲哚-3-羧酸甲酯
• 中文别名: 5-溴-1H-吲哚-3-甲酸甲酯；5-溴-3-吲哚甲酸甲酯
• 英文名称: methyl 5-bromo-1H-indole-3-carboxylate
• 英文别名: 5-bromo-1H-indole-3-carboxylic acid methyl ester；methyl 5-bromoindole-3-carboxylate
• CAS: 773873-77-1
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: MFOKOKHNSVUKON-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C
• 沸点：
  386.2±22.0 °C(Predicted)
• 密度：
  1.629±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 5-Bromoindole-3-carboxylate
Synonyms:

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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: Methyl 5-Bromoindole-3-carboxylate
CAS number: 773873-77-1

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H8BrNO2
Molecular weight: 254.1

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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

制备方法与用途

应用

5-溴吲哚-3-羧酸甲酯可用作有机合成中间体。它可以通过两种途径制备：一是由5-溴-1H-吲哚通过两步反应得到；二是由5-溴-1H-吲哚-3-羧酸通过一步酯化反应获得。

制备

在0℃下，将吡啶（0.30 mL，3.54 mmol）滴加到含有2.72 mmol 5-溴-1H-吲哚的无水THF（6 mL）溶液中。随后，在1小时内向其中逐滴滴加三氯乙酰氯（0.40 mL，3.54 mmol）的THF（6 mL）溶液。反应混合物在室温下搅拌过夜后，用1 M HCl淬灭，并经Na₂SO₄干燥。最后，在真空下浓缩得到粗产品。

将所得固体溶解于MeOH（54 mL）中，加入KOH，加热至回流5小时，然后在环境温度下搅拌1小时。反应混合物再次在真空下浓缩后，通过硅胶色谱法纯化（SiO₂，25％EtOAc/己烷）得到白色固体5-溴吲哚-3-羧酸甲酯。

反应信息

• 作为反应物：
  描述：

  5-溴吲哚-3-羧酸甲酯 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 5-bromo-1-methyl-1H-indole-3-carbohydrazide
  参考文献：
  名称：

  双（吲哚基）三嗪酮，诺托普汀类似物的合成，抗癌评估和分子对接研究

  摘要：

  摘要设计并合成了一系列新的双吲哚基三酮重氮化合物和3,5-双（3'-吲哚基）三嗪酮作为抗癌剂。在体外针对四种不同的人类癌细胞系（如HeLa，MCF-7，MDA-MB-231和A549细胞系）筛选了它们的抗癌活性。其中，化合物17a和17b对人宫颈癌细胞系显示有效的细胞毒性，抑制（IC 50）值分别为4.6和1.3 µM。使用ADT 1.5.6工具进行的计算机模拟研究表明，与其余化合物相比，化合物17b的吲哚环与秋水仙碱活性位点残基Tyr312的独特π-π相互作用可能是其最大效价落后的有效原因，因为其余化合物均具有较高的活性。 图形概要

  DOI：

  10.1007/s11696-017-0372-8
• 作为产物：
  描述：

  在 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 以80%的产率得到5-溴吲哚-3-羧酸甲酯
  参考文献：
  名称：

  锰介导的氧化丙二酸偶联衍生的氮杂富烯中间体的形成和捕获

  摘要：

  使用乙酸锰（III）作为氧化剂进行吲哚/吡咯，丙二酸二甲酯和乙酸的一锅三组分偶联反应。在Mn（OAc）3存在下，吲哚-2和吲哚-3-羰基化合物分别在3-和2-位烷基化，随后在新形成的苄基碳上发生氧化和亲核捕获。相反，2-和3-吲哚羧酸的氧化提供了相应的2-oxindol-3-亚烷基和3-oxindol-2-亚烷基。反应条件，范围和机理在本文中讨论。

  DOI：

  10.1016/j.tet.2016.03.012

文献信息

• [EN] TRIAZOLONE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE TRIAZOLONE ET LEURS UTILISATIONS
  申请人：INCEPTION 2 INC

  公开号：WO2013134562A1

  公开（公告）日：2013-09-12

  The invention disclosed herein is directed to compounds of Formula (I) and pharmaceutically acceptable salts thereof, which are useful in the treatment of prostate, breast, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention also comprises pharmaceutical compositions comprising a therapeutically effective amount of compound of Formula (I), or a pharmaceutically acceptable salt thereof. The invention disclosed herein is also directed to methods of treating prostate, breast, ovarian, liver, kidney, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention disclosed herein is further directed to methods of treating prostate, breast, colon, pancreatic, chronic lymphocytic leukemia, melanoma and other cancers comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist. The compounds and pharmaceutical compositions of the invention are also useful in the treatment of viral infections, such as HCV infections and HIV infections. The invention disclosed herein is also directed to a methods of preventing the onset of and/or recurrence of acute and chronic myeloid leukemia, as well as other cancers, comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist.

  本发明涉及的化合物属于式(I)及其药学上可接受的盐，可用于治疗前列腺、乳腺、结肠、胰腺、人类慢性淋巴细胞白血病、黑色素瘤和其他癌症。该发明还包括含有式(I)化合物的治疗有效量或其药学上可接受的盐的药物组合物。本发明还涉及治疗前列腺、乳腺、卵巢、肝脏、肾脏、结肠、胰腺、人类慢性淋巴细胞白血病、黑色素瘤和其他癌症的方法。本发明还涉及治疗前列腺、乳腺、结肠、胰腺、慢性淋巴细胞白血病、黑色素瘤和其他癌症的方法，包括给予选择性PPARα拮抗剂的治疗有效量。本发明的化合物和药物组合物还可用于治疗病毒感染，如HCV感染和HIV感染。本发明还涉及一种预防急性和慢性骨髓性白血病以及其他癌症发作和/或复发的方法，包括给予选择性PPARα拮抗剂的治疗有效量。
• Heteroaromatic Carboxamide Derivatives as Plasma Kallikrein Inhibitors
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20200054617A1

  公开（公告）日：2020-02-20

  Heteroaromatic carboxamides of formula (I), wherein Y, R, and X are as defined herein, and pharmaceutically acceptable salts thereof. The compounds of formula (I) can be used in methods for the treatment of diseases which can be influenced by inhibition of plasma kallikrein.

  式(I)的杂环芳基羧酰胺，其中Y、R和X如本文所定义，并其药学上可接受的盐。式(I)的化合物可用于治疗受血浆激肽酶抑制影响的疾病的方法。
• Visible light photocatalytic asymmetric synthesis of pyrrolo[1,2-<i>a</i>]indoles <i>via</i> intermolecular [3+2] cycloaddition
  作者：Antonio Casado-Sánchez、Pablo Domingo-Legarda、Silvia Cabrera、José Alemán

  DOI：10.1039/c9cc05838a

  日期：——

  The intermolecular diastereoselective and enantioselective synthesis of pyrrolo[1,2-a]indoles is developed through a [3+2] cycloaddition between silyl-indole derivatives and α,β-unsaturated N-acyl oxazolidinones by merging photocatalysis and Lewis acid catalysis.

  吡咯并[1,2- a ]吲哚的分子间非对映选择性和对映选择性合成是通过甲硅烷基吲哚衍生物与α，β-不饱和N-酰基恶唑烷酮通过光催化和路易斯酸催化的[3 + 2]环加成反应而开发的。
• Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E
  作者：Takumi Abe、Koji Yamada

  DOI：10.1021/acs.orglett.6b03466

  日期：2016.12.16

  We have developed a concise one-pot synthesis of phaitanthrin E derivatives, where simple starting materials undergo an acid-catalyzed intermolecular amination/intramolecular cyclization cascade.

  我们已经开发了一种简单的一锅合成丹黄素E衍生物的方法，其中简单的起始原料会经历酸催化的分子间胺化/分子内环化级联反应。
• Asymmetric Synthesis of 3-Allyloxindoles and 3-Allenyloxindoles by Scandium(III)-Catalyzed Claisen Rearrangement Reactions
  作者：Zeng-Wei Lai、Chuan Liu、Hongbin Sun、Shu-Li You

  DOI：10.1002/cjoc.201700486

  日期：2017.10

  Scandium‐catalyzed asymmetric Claisen rearrangement reactions of 2‐allyloxyindoles and 2‐propargyloxyindoles provide a novel approach to diverse 3‐allyloxindoles and 3‐allenyloxindoles in excellent yields (up to 99%) and enantioselectivity (up to 99% ee) under mild reaction conditions. The scandium catalyst was derived from Sc(OTf)3 and Pybox ligand.

  在温和的反应条件下，催化的2-烯丙氧基吲哚和2-炔丙氧基吲哚的不对称克莱森重排反应提供了一种新颖的方法，以优异的收率（高达99％）和对映选择性（高达ee的99％）对各种3-烯丙氧基吲哚和3-烯丙基氧吲哚进行了反应。 。catalyst催化剂衍生自Sc（OTf）3和Pybox配体。