6-溴-2,3-二氢-1H-吲哚盐酸盐 | 63839-24-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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: 6-溴-2,3-二氢-1H-吲哚盐酸盐
• 中文别名: 6-溴二氢吲哚；6-溴吲哚啉
• 英文名称: 6-bromo-indoline
• 英文别名: 6-bromo-2,3-dihydro-1H-indole；6-Bromoindoline
• CAS: 63839-24-7
• 化学式: C₈H₈BrN
• mdl: MFCD07371638
• 分子量: 198.062
• InChiKey: MTSYZAHZABCWMS-UHFFFAOYSA-N

物化性质

• 沸点：
  116-118 °C(Press: 4 Torr)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromoindoline
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: 6-Bromoindoline
CAS number: 63839-24-7

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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, refrigerated.
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: C8H8BrN
Molecular weight: 198.1

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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

6-溴-2,3-二氢-1H-吲哚盐酸盐可用作有机合成中间体和医药中间体，主要用于实验室研发过程和化工生产过程中。

制备

将TDI01326-1(5.0g，25.64mmol)溶于二氯甲烷(400mL)中，加入三氟乙酸(27.5mL)，然后加入三乙基硅烷(10.5mL，64.1mmol)，在室温下反应16小时。薄层色谱法检测显示反应完全。随后往反应体系中缓慢加入氨水，调节pH值至约9，再加入二氯甲烷(200mL)进行萃取，依次用水(750mL)和饱和食盐水(250mL)洗涤，将有机相用无水硫酸钠干燥后减压浓缩。最后通过柱色谱法分离纯化，得到6-溴-2,3-二氢-1H-吲哚（3.6g，淡黄色油状物）。

反应信息

• 作为反应物：
  描述：

  6-溴-2,3-二氢-1H-吲哚盐酸盐 在 新铜试剂 、 氧气 、 palladium diacetate 作用下， 以 氯苯 为溶剂， 以93 %的产率得到6-溴吲哚
  参考文献：
  名称：

  在无醇盐条件下通过钯 (II) 催化需氧脱氢合成 1H-吲哚、喹啉和 6 元芳香族 N-杂环稠合支架

  摘要：

  开发了一种高效的钯 (II) 催化的饱和N-杂环稠合支架的有氧脱氢反应。该方法无需醇盐即可提供芳香族N-杂环，包括吲哚、喹啉、异喹啉和其他 6 元N-杂环，产率良好至极好（对于 48 个实例，产率高达 99%）。

  DOI：

  10.1002/asia.202100861
• 作为产物：
  描述：

  6-溴吲哚 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以99%的产率得到6-溴-2,3-二氢-1H-吲哚盐酸盐
  参考文献：
  名称：

  N-芳基磺酰二氢吲哚作为视黄酸受体相关孤儿受体 γ (RORγ) 激动剂

  摘要：

  核视黄酸受体相关孤儿受体 γ (RORγ；NR1F3) 是参与 T 辅助细胞 17 ( TH 17) 细胞增殖的炎症基因程序的关键调节因子。因此，针对 RORγ 的合成小分子阻遏剂（反向激动剂）因其作为各种自身免疫性疾病治疗药物的潜力而得到了广泛研究。或者，通过激活（激动）RORγ 增强 T H 17 细胞增殖可能会增强免疫反应，从而为癌症免疫治疗提供一种潜在的新方法。在此，我们描述了N-芳基磺酰二氢吲哚作为 RORγ 激动剂的开发。结构-活性研究揭示了这些分子中的关键连接区域是激动作用的主要决定因素。氢/氘交换与 RORγ-配体复合物的质谱 (HDX-MS) 分析相结合有助于使观察到的结果合理化。

  DOI：

  10.1002/cmdc.201600491
• 作为试剂：
  描述：

  1-(2-fluorophenethyl)piperidin-4-one 、 6-溴-2,3-二氢-1H-吲哚盐酸盐 在 6-溴-2,3-二氢-1H-吲哚盐酸盐 作用下， 以66.6的产率得到1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-bromoindoline
  参考文献：
  名称：

  1,4-substituted cyclic amine derivatives

  摘要：

  下列公式所示的一种新型1,4-取代环氨基衍生物或其药学上可接受的盐：（其中A、B、C、D、T、Y和Z分别代表亚甲基或氮；R1、R2、R3、R4和R5分别代表取代基；n表示0或1至3的整数；m表示0或1至6的整数；p表示1至3的整数。）该化合物具有5-羟色胺受体拮抗作用，并且在临床上可用作药物，特别是用于治疗、改善和预防痉挛性瘫痪或中枢肌肉松弛剂，以改善肌强直症。

  公开号：

  US06448243B1

文献信息

• <i>Ex situ</i> generation of stoichiometric HCN and its application in the Pd-catalysed cyanation of aryl bromides: evidence for a transmetallation step between two oxidative addition Pd-complexes
  作者：Steffan K. Kristensen、Espen Z. Eikeland、Esben Taarning、Anders T. Lindhardt、Troels Skrydstrup

  DOI：10.1039/c7sc03912c

  日期：——

  methodology was also suitable for the synthesis of 13C-labelled benzonitriles with ex situ generated 13C-hydrogen cyanide. Stoichiometric studies with the metal complexes were undertaken to delineate the mechanism for this catalytic transformation. Treatment of Pd(P(tBu)3)2 with H13CN in THF provided two Pd-hydride complexes, (P(tBu)3)2Pd(H)(13CN), and [(P(tBu)3)Pd(H)]2Pd(13CN)4, both of which were isolated

  首次报道了使用接近化学计量和气态氰化氢的钯催化芳基溴化物氰化的方案。采用两室反应器在密闭环境中安全释放异位生成的HCN，事实证明该方法在Ni催化的氢氰化反应中非常有效。随后，利用该装置将一定范围的芳基和杂芳基溴化物（28个实例）直接高产率地转化为相应的苄腈，而无需使用氰化物盐。在二恶烷-水溶剂混合物中，使用Pd（0）预催化剂P（t Bu）3 -Pd-G3和弱碱乙酸钾实现氰化。该方法也适用于13的合成C-标记的苄腈与异位生成13 C-氰化氢。进行了金属配合物的化学计量研究，以描述这种催化转化的机理。在THF中用H 13 CN处理Pd（P（t Bu）3）2提供了两种Pd-氢化物配合物（P（t Bu）3）2 Pd（H）（13 CN）和[（P（t Bu） ）3）Pd（H）] 2 Pd（13 CN）4，两者均已分离，并通过NMR光谱和X射线晶体结构分析进行了表征。当在KOAc存在下在THF∶水混合物中进行相同的反应时，仅形成（P（t
• Ru(<scp>ii</scp>)-Catalyzed C7-acyloxylation of indolines with carboxylic acids
  作者：Pinaki Bhusan De、Sonbidya Banerjee、Sourav Pradhan、Tharmalingam Punniyamurthy

  DOI：10.1039/c8ob01603h

  日期：——

  Ruthenium-catalyzed site-selective C7-acyloxyation of indolines with carboxylic acids is presented that can be oxidized to indoles with diverse functional groups.

  铑催化的选择性C7-酰氧化反应将吲哚与羧酸进行作用，可氧化为具有多种功能基团的吲哚化合物。
• A Unified Approach to Couple Aromatic Heteronucleophiles to Azines and Pharmaceuticals
  作者：Ryan G. Anderson、Brianna M. Jett、Andrew McNally

  DOI：10.1002/anie.201807322

  日期：2018.9.17

  Coupling aromatic heteronucleophiles to arenes is a common way to assemble drug‐like molecules. Many methods operate via nucleophiles intercepting organometallic intermediates, via Pd‐, Cu‐, and Ni‐catalysis, that facilitate carbon‐heteroatom bond formation and a variety of protocols. We present an alternative, unified strategy where phosphonium salts can replicate the behavior of organometallic intermediates

  将芳香族异核试剂与芳烃偶联是组装类药物分子的常见方法。许多方法通过亲核试剂拦截有机金属中间体，通过 Pd、Cu 和 Ni 催化来进行，从而促进碳杂原子键的形成和各种方案。我们提出了一种替代的、统一的策略，其中鏻盐可以复制有机金属中间体的行为。在一组狭窄的反应条件下，多种芳香族杂核亲核试剂可以与吡啶和二嗪偶联，这在金属催化偶联中经常出现问题，例如在具有多个极性官能团的复杂结构中无法获得（假）卤化物前体。
• INDOLE CARBOXAMIDE COMPOUNDS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160115126A1

  公开（公告）日：2016-04-28

  Disclosed are compounds of Formula (I): or a salt thereof, wherein: X is CR 4 or N; R 1 , R 2 , R 3 , R 4 , and A are defined herein. Also disclosed are methods of using such compounds as inhibitors of Bruton's tyrosine kinase (Btk), and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  揭示了Formula (I)的化合物： 或其盐，其中：X为CR 4 或N；R 1 ，R 2 ，R 3 ，R 4 和A在此处定义。还揭示了使用这些化合物作为Bruton's酪氨酸激酶（Btk）抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓各种治疗领域的疾病或疾病的进展方面非常有用，如自身免疫疾病和血管疾病。
• Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-<i>a</i>]indoles
  作者：Honggui Huang、Menglin Yu、Xiaolong Su、Peng Guo、Jia Zhao、Jiabing Zhou、Yi Li

  DOI：10.1021/acs.joc.7b03017

  日期：2018.2.16

  We disclose herein a photocatalytic difluoroalkylation and cyclization cascade reaction of N-(but-2-enoyl)indoles with broad substrate scopes in up to 90% isolated yield. This method provides sustainable and efficient access to synthesize difluoroalkylated pyrrolo[1,2-a]indoles with a quaternary carbon center under mild conditions.

  我们在此公开了N-（丁-2-烯酰基）吲哚具有宽的底物范围的光催化二氟烷基化和环化级联反应，其分离产率高达90％。该方法提供了在温和条件下可持续有效地合成具有季碳中心的二氟烷基化吡咯并[1,2- a ]吲哚的方法。