2-氟吡啶-3-硼酸频哪酯 | 452972-14-4

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氟吡啶-3-硼酸频哪酯
• 中文别名: 2-氟吡啶-3-硼酸频哪醇酯；2-氟吡啶-3-硼酸频那醇酯；2-氟-3-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶；2-氟嘧啶-3-硼酸频那醇酯
• 英文名称: 2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• 英文别名: 2-fluoropyridine-3-boronic acid pinacol ester
• CAS: 452972-14-4
• 化学式: C₁₁H₁₅BFNO₂
• mdl: MFCD06798245
• 分子量: 223.055
• InChiKey: YYOZFGQOPNTVGM-UHFFFAOYSA-N

物化性质

• 熔点：
  42-45°C
• 沸点：
  309.9±27.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  按规定使用和贮存不会分解，避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• TSCA：
  No
• 危险等级：
  IRRITANT
• 安全说明：
  S26,S37
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Fluoropyridine-3-boronic acid, pinacol ester
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

---

Section 3. Composition/information on ingredients.
2-Fluoropyridine-3-boronic acid, pinacol ester
Ingredient name:
CAS number: 452972-14-4

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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, 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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C11H15BFNO2
Molecular weight: 223.1

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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 fluoride.

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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：

  2-氟吡啶-3-硼酸频哪酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三氟化硼乙醚 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.34h， 生成 1-(1-(2-fluoropyridin-3-yl)cyclopropyl)ethanone
  参考文献：
  名称：

  环戊烯酮的氧化环收缩：环丙基酮的一般方法，包括机理的见解。

  摘要：

  报道了在大气条件下易于形成环丙基酮（CPK）的易获得的环丁烯衍生物的原始氧化环收缩。建议进行全面的机械研究以支持这种新颖但又不寻常的重排。对该机理的见解最终导致使用m简化和泛化环丁烯的环收缩CPBA作为氧化剂。这种独特且具有官能团耐受性的转化是在室温下于温和条件下进行的，从而提供了一个新的多官能基序文库。由于CPK是吸引人的和特权的药效团，这种简单明了的策略的阐述代表了用于药物发现和药物化学的极有价值的工具。另外，所描述的方法被用于以最少的步骤生成生物活性物质和关键前体的库。

  DOI：

  10.1021/acs.joc.8b00297
• 作为产物：
  描述：

  2-氟吡啶 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 2-氟吡啶-3-硼酸频哪酯
  参考文献：
  名称：

  定向邻位金属化，硼化和吡啶类化合物的铃木-宫浦交叉耦合：一锅议定书替补Azabiaryls ＃

  摘要：

  描述了通过一锅法合成氮杂双芳基化合物19a - t的一般方法，该方法涉及定向原金属化（D o M）-硼化-铃木-宫浦交叉偶联序列。除了三种异构的吡啶基羧酰胺15a - c外，氯-，氟-和O-氨基甲酰基吡啶也适用于该方法，提供了一系列的氮杂双芳基（表2）。该方法的优点在于，避免了公认的吡啶基硼酸的分离困难及其对脱硼的不稳定性。hydroxypicolinamides的有效合成12 - 14（方案3）通过LDA-B（O i）的一锅金属化-硼化-氧化顺序PR）3原位避免初期的自缩合过程邻-metalated物种（方案2）是描绘。证明了通过定向远程金属化方案将氮杂双芳基19b，e，h，l转化为氮杂芴酮20b，e，h，l（表3）。给出了对当代杂环合成化学相当感兴趣的硼酸吡啶基酯的综合研究结果（图1）。

  DOI：

  10.1021/jo0620359

文献信息

• [EN] INHIBITORS OF THE WNT SIGNALLING PATHWAYS<br/>[FR] INHIBITEURS DES VOIES DE SIGNALISATION WNT
  申请人：BAYER PHARMA AG

  公开号：WO2015140196A1

  公开（公告）日：2015-09-24

  The present invention relates to inhibitors of the Wnt signalling pathways of general formula (I) as described and defined herein, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of a hyper- proliferative disorder, as a sole agent or in combination with other active ingredients.

  本发明涉及通式（I）所述和定义的Wnt信号通路抑制剂，涉及制备该类化合物的方法，有用于制备该类化合物的中间化合物，包含该类化合物的药物组合物和组合物，以及利用该类化合物制造用于治疗或预防疾病的药物组合物，特别是用作唯一药剂或与其他活性成分组合使用时，用于治疗或预防过度增殖性疾病。
• Iridium-catalyzed C–H borylation of pyridines
  作者：Scott A. Sadler、Hazmi Tajuddin、Ibraheem A. I. Mkhalid、Andrei S. Batsanov、David Albesa-Jove、Man Sing Cheung、Aoife C. Maxwell、Lena Shukla、Bryan Roberts、David C. Blakemore、Zhenyang Lin、Todd B. Marder、Patrick G. Steel

  DOI：10.1039/c4ob01565g

  日期：——

  The iridium-catalysed C–H borylation is a valuable and attractive method for the preparation of aryl and heteroaryl boronates. However, application of this methodology for the preparation of pyridyl and related azinyl boronates can be challenged by low reactivity and propensity for rapid protodeborylation, particularly for a boronate ester ortho to the azinyl nitrogen. Competition experiments have revealed that the low reactivity is due to inhibition of the active catalyst through coordination of the azinyl nitrogen lone pair at the vacant site on the iridium. This effect can be overcome through the incorporation of a substituent at C-2. Moreover, when this is sufficiently electron-withdrawing protodeborylation is sufficiently slowed to permit isolation and purification of the C-6 boronate ester. Following functionalization, reduction of the directing C-2 substituent provides the product arising from formal ortho borylation of an unhindered pyridine ring.

  铱催化的C-H硼化是一种有价值且有吸引力的方法，用于制备芳基和杂芳基硼酸酯。然而，这种方法在制备吡啶基及相关氮杂基硼酸酯时可能面临反应活性低和快速质子脱硼化的挑战，尤其是当硼酸酯位于氮杂基氮原子的邻位时。竞争实验揭示，低反应活性是由于氮杂基氮原子的孤对电子在铱的空位上配位，抑制了活性催化剂。通过在C-2位引入取代基可以克服这一效应。此外，当该取代基足够吸电子时，质子脱硼化过程会被足够减缓，从而允许分离和纯化C-6硼酸酯。经过功能化后，导向C-2取代基的还原提供了源自未受阻吡啶环形式邻位硼化的产物。
• Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters
  作者：Alexandre Bouillon、Jean-Charles Lancelot、Valérie Collot、Philippe R Bovy、Sylvain Rault

  DOI：10.1016/s0040-4020(02)00283-1

  日期：2002.4

  This paper describes a general method for the synthesis and the isolation of novel 2,4, or 5-halopyridin-3-yl-boronic acids and esters 4, 7, 10, 13, 15. These compounds are prepared taking into account a regioselective halogen–metal exchange using nBuLi or a regioselective ortho-lithiation using lithium diisopropylamide and subsequent quenching with triisopropylborate starting from appropriate mono

  本文描述了用于合成和5-卤代吡啶-3-基-硼酸酯的一般方法的新的2,4-隔离，或和4，7，10，13，15。这些化合物的制备考虑了使用n BuLi进行的区域选择性卤素-金属交换或区域选择性邻位交换-使用二异丙基氨基锂进行锂化，然后从适当的单或二卤代吡啶开始，用硼酸三异丙基酯淬灭。迄今为止研究的所有底物均提供单一的区域异构硼酸或酯产物。另外，已经发现这些化合物与一系列的芳基卤化物进行了Pd催化的偶联，并授权了一种制备新吡啶文库的策略。
• [EN] INDAZOLE COMPOUNDS AS IRAK4 INHIBITORS<br/>[FR] COMPOSÉS D'IMIDAZOLE UTILISABLES EN TANT QU'INHIBITEURS DE L'IRAK4
  申请人：AURIGENE DISCOVERY TECH LTD

  公开号：WO2015104662A1

  公开（公告）日：2015-07-16

  The present invention provides indazole compound of formula (I), which are therapeutically useful as kinase inhibitor, particularly IRAK4 inhibitors. wherein Z1, Z2, R1, R2, R3, 'm' and 'n' have the meanings given in the specification, and pharmaceutically acceptable salts or stereoisomers thereof that are useful in the treatment and prevention of diseases or disorder, in particular their use in diseases or disorder mediated by kinase enzyme, particularly IRAK4 enzyme. The present invention also provides pharmaceutical composition comprising at least one of the compounds of compound of formula (I) together with a pharmaceutically acceptable carrier, diluent or excipient therefor.

  本发明提供了式（I）的吲唑化合物，其在治疗中具有潜在的激酶抑制作用，特别是IRAK4抑制剂。其中Z1、Z2、R1、R2、R3、'm'和'n'的含义如规范中所述，并且其药学上可接受的盐或立体异构体在治疗和预防疾病或紊乱方面具有用处，特别是在由激酶酶介导的疾病或紊乱中的应用，特别是IRAK4酶。本发明还提供了包括至少一种式（I）化合物的药物组合物，以及药学上可接受的载体、稀释剂或赋形剂。
• [EN] KINASE MODULATING COMPOUNDS, COMPOSITIONS CONTAINING THE SAME AND USE THEREOF<br/>[FR] COMPOSÉS MODULANT UNE KINASE, COMPOSITIONS LES CONTENANT ET UTILISATION DE CEUX-CI
  申请人：CENTAURUS BIOPHARMA CO LTD

  公开号：WO2013071865A1

  公开（公告）日：2013-05-23

  The invention provides a compound represented by formula (I) which may modulate a kinase, and a pharmaceutical composition thereof, as well as the method for preventing or treating a protein kinase mediated disease or condition.

  该发明提供了一种由式(I)表示的化合物，可以调节激酶，以及其药物组合物，以及预防或治疗蛋白激酶介导的疾病或病况的方法。