1H-吡咯并[2,3-B]吡啶-3-羧酸甲酯 | 808137-94-2

• 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 - 吡咯并吡啶类
• 中文名称: 1H-吡咯并[2,3-B]吡啶-3-羧酸甲酯
• 中文别名: 7-氮杂吲哚-3-甲酸甲酯；7-氮杂吲哚-3-羧酸甲酯
• 英文名称: methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate
• 英文别名: methyl 7-azaindole-3-carboxylate
• CAS: 808137-94-2
• 化学式: C₉H₈N₂O₂
• mdl: MFCD09864656
• 分子量: 176.175
• InChiKey: XYRUNIAHPKBUJT-UHFFFAOYSA-N

物化性质

• 熔点：
  57-59℃
• 密度：
  1.324

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Methyl 1h-pyrrolo[2,3-b]pyridine-3-carboxylate
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Methyl 1h-pyrrolo[2,3-b]pyridine-3-carboxylate
Ingredient name:
CAS number: 808137-94-2

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H8N2O2
Molecular weight: 176.2

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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.

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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

用途

1H-吡咯并[2,3-b]吡啶-3-羧酸甲酯是一种羧酸酯类衍生物，可用作有机合成中的中间体。它在医药、食品、农药和日用化学品等领域拥有广泛的应用。

合成路线

1H-吡咯并[2,3-b]吡啶-3-羧酸甲酯的合成反应式如下图：

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  1H-吡咯并[2,3-b]吡啶-3-甲酸	1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid	156270-06-3	C8H6N2O2	162.148
  2,2,2-三氯-1-(1H-吡咯并[2,3-b]吡啶-3-基)-乙酮	2,2,2-trichloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone	163220-69-7	C9H5Cl3N2O	263.51
  3-氰基-7-氮杂吲哚	3-cyano-7-azaindole	4414-89-5	C8H5N3	143.148
  1-苯磺基-1H-吡咯并[2,3-B]吡啶-3-甲酸甲基酯	1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester	245064-81-7	C15H12N2O4S	316.337

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 1-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate	——	C14H11N3O2	253.26
  ——	1H-pyrrolo[2,3-b]pyridine-3-carbohydrazide	310887-39-9	C8H8N4O	176.178
  ——	methyl 1-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate	——	C14H11N3O2	253.26
  ——	1-(4-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid	——	C15H11FN2O2	270.263
  ——	methyl 1-(thiazol-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate	——	C12H9N3O2S	259.29

反应信息

• 作为反应物：
  描述：

  1H-吡咯并[2,3-B]吡啶-3-羧酸甲酯 在 肼 作用下， 以 甲醇 、 水 为溶剂， 反应 21.0h， 生成 1H-pyrrolo[2,3-b]pyridine-3-carbohydrazide
  参考文献：
  名称：

  [EN] OXADIAZOLE DERIVATIVES AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS
  [FR] DÉRIVÉS D'OXADIAZOLE ET LEUR UTILISATION COMME MODULATEURS DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE

  摘要：

  Oxadiazole衍生物的化学式（I），其中环A是一个双环或三环系统。所述化合物对尼古丁型乙酰胆碱受体（nAChRs）具有活性，并可用于治疗神经系统、精神病学和胃肠道疾病，以及败血症和肥胖症。

  公开号：

  WO2009071577A1
• 作为产物：
  描述：

  3-氰基-7-氮杂吲哚 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以87.6%的产率得到1H-吡咯并[2,3-B]吡啶-3-羧酸甲酯
  参考文献：
  名称：

  一种7-氮杂吲哚-3-甲酸甲酯的合成方法

  摘要：

  本发明公开了一种7‑氮杂吲哚‑3‑甲酸甲酯的合成方法，属于有机合成领域。本发明以2‑氨基‑3‑溴吡啶为反应物，在酸性环境下与3‑羟基丙烯腈金属盐反应合成3‑（3‑溴吡啶‑2‑基氨基）丙烯腈，把3‑（3‑溴吡啶‑2‑基氨基）丙烯腈，碱，催化体系加入到溶剂中，反应生成3‑氰基‑7‑氮杂吲哚，最后在甲醇和盐酸的存在下反应得7‑氮杂吲哚‑3‑甲酸甲酯。本发明原料廉价易得，反应步骤简单，反应条件温和，产品质量稳定，纯度高，适合工业化生产。

  公开号：

  CN106588921B

文献信息

• [EN] HEPARANASE INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS D'HÉPARANASE ET LEUR UTILISATION
  申请人：BETA THERAPEUTICS PTY LTD

  公开号：WO2018107200A1

  公开（公告）日：2018-06-21

  The invention relates to functionalized quinazoline compounds, pharmaceutical compositions comprising such compounds, and the use of such compounds as heparanase inhibitors for the treatment of diseases or conditions related to heparanse activity.

  本发明涉及功能化喹唑啉化合物，包括此类化合物的药物组合物，以及此类化合物作为肝素酶抑制剂用于治疗与肝素酶活性相关的疾病或状况的使用。
• [EN] THERAPEUTIC INHIBITORY COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS THÉRAPEUTIQUES
  申请人：LIFESCI PHARMACEUTICALS INC

  公开号：WO2018011628A1

  公开（公告）日：2018-01-18

  Provided herein are heterocyclic derivative compounds and pharmaceutical compositions comprising said compounds that are useful for inhibiting plasma kallikrein. Furthermore, the subject compounds and compositions are useful for the treatment of diseases wherein the inhibition of plasma kallikrein inhibition has been implicated, such as angioedema and the like.

  本文提供了杂环衍生物化合物和包含这些化合物的药物组合物，用于抑制血浆激肽酶。此外，这些化合物和组合物对于治疗血浆激肽酶抑制已被证实有关的疾病，如血管性水肿等，具有益处。
• [EN] [4[4-(5-AMINOMETHYL-2-FLUORO-PHENYL)-PIPERIDIN-1-YL]-(1H-PYRROLO-PYRIDIN-YL)-METHANONES AND SYNTHESIS THEREOF<br/>[FR] [4[4-(5-AMINOMÉTHYL-2-FLUORO-PHÉNYL)-PIPÉRIDIN-1-YL]-(1H-PYRROLO-PYRIDIN-YL)-MÉTHANONES ET LEUR SYNTHÈSE
  申请人：SANOFI SA

  公开号：WO2011078984A1

  公开（公告）日：2011-06-30

  The present invention relates herein to compounds and compositions for the treatment and amelioration of inflammatory disease. Specifically the present invention relates to compounds that having a tryptase inhibition activity and the intermediates thereof, pharmaceutical compositions comprising such compounds, and a method of treating subjects suffering from a condition disease or disorder that can be ameliorated by the administration of an inhibitor of tryptase including but not limited to for example asthma and other inflammatory diseases including age-related macular degeneration.

  本发明涉及用于治疗和改善炎症性疾病的化合物和组合物。特别是，本发明涉及具有胰蛋白酶抑制活性的化合物及其中间体，包括这些化合物的药物组合物，以及治疗可通过施用胰蛋白酶抑制剂来改善的状况、疾病或失调的方法，例如但不限于哮喘和其他炎症性疾病，包括年龄相关的黄斑变性。
• [EN] SPIROHEPTANE SALICYLAMIDES AND RELATED COMPOUNDS AS INHIBITORS OF ROCK<br/>[FR] SALICYLAMIDES DE SPIROHEPTANE ET COMPOSÉS ASSOCIÉS UTILISÉS COMME INHIBITEURS DE ROCK
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2017123860A1

  公开（公告）日：2017-07-20

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically-acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了式(I)的化合物：或立体异构体、互变异构体或药用可接受的盐，其中所有变量如本文所述定义。这些化合物是选择性的ROCK抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用同一化合物治疗心血管、平滑肌、肿瘤学、神经病理学、自身免疫、纤维化和/或炎症性疾病的方法。
• [EN] 5-HT3 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RÉCEPTEUR 5-HT3
  申请人：ENVOY THERAPEUTICS INC

  公开号：WO2014014951A1

  公开（公告）日：2014-01-23

  The present invention provides 5-HT3 receptor antagonists of Formula (I): which are useful for the treatment of diseases treatable by inhibition of 5-HT3 receptor such as emesis, pain, drug addiction, neurodegenerative and psychiatric disorders, and GI disorders. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  本发明提供了式(I)的5-HT3受体拮抗剂，用于治疗通过抑制5-HT3受体可治疗的疾病，如呕吐、疼痛、药物成瘾、神经退行性和精神障碍以及胃肠道疾病。还提供了含有这类化合物的药物组合物和制备这类化合物的方法。