1-BOC-3-碘-7-氮杂吲哚 | 192189-18-7

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 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: 1-BOC-3-碘-7-氮杂吲哚
• 中文别名: 3-碘吡咯并[2,3-B]吡啶-1-羧酸叔丁酯；1H-吡咯[2,3-B]吡啶-1-羧酸-3-碘-1,1-二甲基乙酯
• 英文名称: tert-butyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate
• 英文别名: tert-butyl 3-iodopyrrolo[2,3-b]pyridine-1-carboxylate
• CAS: 192189-18-7
• 化学式: C₁₂H₁₃IN₂O₂
• mdl: MFCD08741526
• 分子量: 344.152
• InChiKey: YNWXYUIDHAWPLF-UHFFFAOYSA-N

物化性质

• 熔点：
  79℃
• 沸点：
  397.3±45.0 °C(Predicted)
• 密度：
  1.65

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：
  0.333
• 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
• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存储条件：密封、干燥、避光，适宜温度为2-8°C。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 1-Boc-3-iodo-7-azaindole
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 1-Boc-3-iodo-7-azaindole
CAS number: 192189-18-7

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C12H13IN2O2
Molecular weight: 344.1

---

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 Iodide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-BOC-3-碘-7-氮杂吲哚 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium acetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 [5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiophen-2-ylmethyl]-carbamic acid tert-butyl ester trifluoroacetic acid salt
  参考文献：
  名称：

  WO2008/5457

  摘要：

  公开号：
• 作为产物：
  描述：

  7-氮杂吲哚 在 4-二甲氨基吡啶 、 碘 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 1-BOC-3-碘-7-氮杂吲哚
  参考文献：
  名称：

  新型美林素衍生物作为快速的细胞凋亡诱导剂。

  摘要：

  具有多激酶抑制剂活性的3-（杂）芳基取代的7-氮杂吲哚可通过一锅增田（Masuda）硼酸酯化-铃木偶联序列容易地获得。几种有前途的衍生物被确定为凋亡诱导剂，并强调了多激酶的抑制潜力，为鞘氨醇激酶2抑制剂。我们的测量结果提供了对美丽素衍生物的结构-活性关系的更多见解，表明带有吡啶部分带有2位氨基的吡啶部分的衍生物是最有活性的抗癌化合物，因此是未来体内研究的极有希望的候选者。

  DOI：

  10.1016/j.bmc.2019.06.029

文献信息

• Synthesis and biological evaluation of novel macrocyclic bis-7-azaindolylmaleimides as potent and highly selective glycogen synthase kinase-3β (GSK-3β) inhibitors
  作者：Lan Shen、Catherine Prouty、Bruce R. Conway、Lori Westover、Jun Z. Xu、Richard A. Look、Xin Chen、Mary Pat Beavers、Jerry Roberts、William V. Murray、Keith T. Demarest、Gee-Hong Kuo

  DOI：10.1016/j.bmc.2003.09.047

  日期：2004.3

  that resulted in the synthesis of novel series of macrocyclic bis-7-azaindolylmaleimides. Among the three series of macrocycles, the oxygen atom and thiophene containing linkers yielded molecules with higher inhibitory potency at GSK-3 beta (K(i)=0.011-0.079 microM) while the nitrogen atom containing linkers yielded molecules with lower potency (K(i)=0.150->1 microM). Compound 33 and 36 displayed 1-2

  钯催化的交叉偶联反应用于合成两个关键中间体3和5，从而导致合成了一系列新的大环双7-氮杂吲哚基马来酰亚胺。在这三个系列的大环中，含氧原子和噻吩的连接子在GSK-3 beta处具有更高的抑制力（K（i）= 0.011-0.079 microM），而含氮原子的连接子则具有较低的抑制力（K（ i）= 0.150-> 1 microM）。化合物33和36在GSK-3 beta对CDK2，PKC beta II，Rsk3表现出1-2个数量级的选择性，对其他62种蛋白激酶的抑制作用很小或没有抑制作用。与PKC beta II相比，化合物46对GSK-3 beta的选择性至少高100倍，并且对65种蛋白激酶几乎没有或没有活性，几乎表现为GSK-3 beta' 特异性抑制剂”。这三种化合物在GS测定中均显示出良好的效价。进行分子对接研究，以试图使氮杂吲哚基马来酰亚胺的GSK-3β选择性合理化。这些非冠醚型
• Rapid synthesis of bis(hetero)aryls by one-pot Masuda borylation–Suzuki coupling sequence and its application to concise total syntheses of meridianins A and G
  作者：Eugen Merkul、Elisabeth Schäfer、Thomas J. J. Müller

  DOI：10.1039/c1ob05310h

  日期：——

  3-(Hetero)aryl substituted indoles, 7-azaindoles, and pyrroles can be obtained in a very concise fashion via a one-pot Masuda borylation–Suzuki coupling sequence. The concise total syntheses of the marine natural products meridianins A (5) and G (4i) nicely illustrate the utility of this methodology.

  通过一锅增田（Masuda）硼酸酯化-铃木（Suzuki）偶联序列可以非常简明的方式获得3-（杂）芳基取代的吲哚，7-氮杂吲哚和吡咯。海洋天然产物子午线素A（5）和G（4i）的简洁的总合成很好地说明了该方法的实用性。
• Sustainable Fe–ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water
  作者：Sachin Handa、Ye Wang、Fabrice Gallou、Bruce H. Lipshutz

  DOI：10.1126/science.aac6936

  日期：2015.9.4

  1087 An iron preparation substantially lowers the quantity of palladium needed to catalyze a common reaction that forms C-C bonds. Most of today’s use of transition metal–catalyzed cross-coupling chemistry relies on expensive quantities of palladium (Pd). Here we report that nanoparticles formed from inexpensive FeCl3 that naturally contains parts-per-million (ppm) levels of Pd can catalyze Suzuki-Miyaura

  铁为痕量钯提供动力 钯 (Pd) 是化学催化的支柱。贵金属具有锻造碳-碳 (CC) 键的诀窍。汉达等人。现在报告说，当与铁混合在特定制剂中时，仅百万分之一的 Pd 就足以催化形成 CC 键的 Suzuki 偶联反应。表面活性剂的加入使反应在水中进行。该协议预示着在药物和农用化学品合成中保护 Pd 是个好兆头。科学，这个问题 p。1087 铁制剂显着降低了催化形成 CC 键的常见反应所需的钯量。今天大多数过渡金属催化交叉偶联化学的使用依赖于昂贵数量的钯 (Pd)。在这里，我们报告说，由天然含有百万分之一 (ppm) 水平 Pd 的廉价 FeCl3 形成的纳米粒子可以催化 Suzuki-Miyaura 反应，包括涉及极具挑战性的反应伙伴的情况。纳米胶束用于溶解反应物并将反应伙伴传递给 Fe-ppm Pd 催化剂，从而形成碳-碳键。新形成的催化剂可以在环境温度下分离和储存。含有表面活性剂和催化剂
• One-Pot Synthesis of Diazine-Bridged Bisindoles and Concise Synthesis of the Marine Alkaloid Hyrtinadine A
  作者：Boris O. A. Tasch、Eugen Merkul、Thomas J. J. Müller

  DOI：10.1002/ejoc.201100680

  日期：2011.8

  N-Boc-protected 3-iodoindoles and 3-iodo-7-azaindole in a pseudo three-component reaction involving a one-pot Masuda borylation–Suzuki arylation sequence. Some of the title compounds display promising cytotoxic properties. The versatility of this methodology is illustrated by a very concise total synthesis of the marine alkaloid hyrtinadine A.

  二嗪桥连的双吲哚很容易从 N-Boc 保护的 3-碘代吲哚和 3-碘-7-氮杂吲哚在伪三组分反应中获得，该反应涉及一锅 Masuda 硼酸化 - Suzuki 芳基化序列。一些标题化合物显示出有希望的细胞毒性特性。海洋生物碱 hyrtinadine A 的非常简洁的全合成说明了这种方法的多功能性。
• [EN] HETEROARYL COMPOUNDS FOR KINASE INHIBITION<br/>[FR] COMPOSÉS HÉTÉROARYLE D'INHIBITION DE LA KINASE
  申请人：ARIAD PHARMA INC

  公开号：WO2015195228A1

  公开（公告）日：2015-12-23

  Compounds and pharmaceutical compositions that modulate kinase activity, including mutant EGFR and mutant HER2 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including mutant EGFRand mutant HER2 activity, are described herein.

  调节激酶活性的化合物和药物组合物，包括突变的EGFR和突变的HER2激酶活性，以及与激酶活性相关的疾病和病况的治疗方法、化合物、药物组合物，包括突变的EGFR和突变的HER2活性，均在本文中描述。