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What are the chemical properties of 3-Iodo-1H-pyrrolo [2,3-b] pyridine
3-Iodine-1H-pyrrolido [2,3-b] pyridine is an organic compound. Its chemical properties are unique and worthy of investigation.
First of all, the iodine atom in this compound gives it a certain reactivity. The iodine atom is relatively large and has strong electronegativity. In nucleophilic substitution reactions, it can be replaced by other nucleophiles as a leaving group. For example, under appropriate basic conditions, nucleophiles containing hydroxyl groups, amino groups, etc. can react with the compound, and the iodine atoms leave to form new derivatives containing different functional groups.
Furthermore, the dense ring structure of pyrrolido [2,3-b] pyridine gives the molecule a special electron cloud distribution. The pyridine ring part has a certain alkalinity. Due to the presence of lone pair electrons on the nitrogen atom, it can react with protons or other electrophilic reagents. The pyrrole ring is electron-rich and prone to electrophilic substitution reactions, especially at the α-position of the pyrrole ring, the electron cloud density is relatively high, and electrophilic reagents are more likely to attack here.
In addition, this compound also has characteristics in redox reactions. The unsaturated bonds in its molecular structure and the nitrogen atom can undergo corresponding oxidation or reduction reactions under the action of suitable oxidants or reducing agents, thereby changing the structure and properties of the molecule. At the same time, due to the existence of its conjugated system, it may also show unique photophysical properties, such as may have certain fluorescence properties. Under the irradiation of light of a specific wavelength, the molecule absorbs energy and then undergoes electronic transition, and then releases energy in the form of fluorescence.
Overall, the chemical properties of 3-iodine-1H-pyrrolido [2,3-b] pyridine are rich and diverse, and have potential application value in organic synthesis, pharmaceutical chemistry and other fields. It can be used as a key intermediate to construct more complex organic molecular structures.
What is the common synthesis method of 3-Iodo-1H-pyrrolo [2,3-b] pyridine?
3-Iodine-1H-pyrrolido [2,3-b] pyridine is an important intermediate in the field of organic synthesis. Its common synthesis methods are multi-terminal, and the following is detailed by you.
The halogenation method using pyrrolido [2,3-b] pyridine as the starting material is first recommended. This approach requires pyrrolido [2,3-b] pyridine to interact with iodine under appropriate reaction conditions. Common iodine sources such as iodine elemental ($I_2 $), N-iodosuccinimide (NIS), etc. If the iodine element is used as the iodine source, it is often necessary to add an appropriate oxidant, such as hydrogen peroxide ($H_2O_2 $) or nitric acid ($HNO_3 $), to promote the reaction. The reaction mechanism is roughly that the oxidant oxidizes the iodine element to a more active iodine cation ($I ^ + $), and then the iodine cation initiates an electrophilic substitution reaction at a specific position of pyrrolido [2,3-b] pyridine to generate 3-iodine-1H-pyrrolido [2,3-b] pyridine.
Furthermore, it can be achieved through a coupling reaction catalyzed by a transition metal. For example, using halogenated pyridine or pyridyl boric acid derivatives containing suitable substituents as raw materials, with the help of transition metal catalysts such as palladium ($Pd $) and copper ($Cu $), the coupling reaction with iodide reagents occurs under basic conditions. Among them, palladium-catalyzed coupling reactions are widely used. In typical palladium-catalyzed reaction systems, palladium complexes such as tetra (triphenylphosphine) palladium ($Pd (PPh_3) _4 $) are often used as catalysts, and potassium carbonate ($K_2CO_3 $) and sodium carbonate ($Na_2CO_3 $) are used as bases. During the reaction, the halogenated pyridine or pyridyl boronic acid derivative first undergoes oxidative addition reaction with palladium catalyst to form a palladium intermediate, and then the intermediate undergoes metal transfer and reduction elimination reactions with the iodide reagent, and finally generates the target product 3-iodine-1H-pyrrolido [2,3-b] pyridine.
In addition, there are some synthesis strategies based on intramolecular cyclization. Using a chain or cyclic precursor compound with a specific structure as the starting material, a pyrrolido [2,3-b] pyridine skeleton is constructed through intramolecular cyclization reaction, and iodine atoms are introduced at the same time. This method often requires ingenious design of the structure of the precursor compound and selection of appropriate reaction conditions to achieve efficient cyclization and iodine substitution processes.
In summary, the synthesis methods of 3-iodine-1H-pyrrolido [2,3-b] pyridine are diverse. In practical applications, it is necessary to choose the most suitable synthesis path according to many factors such as the availability of raw materials, the difficulty of controlling the reaction conditions, and the purity requirements of the target product.
In which fields is 3-Iodo-1H-pyrrolo [2,3-b] pyridine used?
3-Iodine-1H-pyrrolido [2,3-b] pyridine is useful in many fields such as medicine and materials science.
In the field of medicine, it is the backbone of organic synthesis. By skillfully splicing different chemical groups, various new drug molecules can be created. What is particularly striking is that in the development of anti-cancer drugs, 3-iodine-1H-pyrrolido [2,3-b] pyridine has shown significant inhibitory activity on specific cancer cells due to its unique chemical structure. Researchers hope to use this as a basis to carve out anti-cancer drugs with better efficacy and less side effects. For example, by precisely modifying its structure, regulating the interaction with cancer cell targets, and improving the targeting of drugs, it can more effectively kill cancer cells and bring new hope to cancer patients.
In the field of materials science, this compound has also made a name for itself. Due to its unique electronic and optical properties, it has shown great potential in the field of organic optoelectronic materials. It can be carefully prepared into organic semiconductor materials for use in organic Light Emitting Diodes (OLEDs) and organic solar cells. In the field of OLEDs, it can effectively improve the luminous efficiency and stability of devices, laying the foundation for the manufacture of high-resolution, high-contrast and energy-saving displays. In the field of organic solar cells, it helps to improve the absorption and charge transfer efficiency of light, promote the direction of higher conversion efficiency of solar cells, and promote the wide application and development of clean energy.
What is the market outlook for 3-Iodo-1H-pyrrolo [2,3-b] pyridine?
3-Iodo-1H-pyrrolo [2,3-b] pyridine is an organic compound with potential application value in the fields of medicinal chemistry and materials science. Its market prospect is promising for the following reasons:
###Pharmaceutical R & D
1. ** Anti-cancer drug development **: Many studies have shown that compounds containing pyridine and pyrrole structures exhibit inhibitory activity on cancer cell growth. The unique chemical structure of 3-Iodo-1H-pyrrolo [2,3-b] pyridine may be used as a key intermediate for the synthesis of new anti-cancer drugs. With the increasing incidence of cancer, the market demand for anti-cancer drugs continues to grow, bringing broad opportunities for it. For example, a research team used this compound as a starting material to synthesize a drug molecule targeting specific cancer cell receptors through a series of reactions, which showed good anti-cancer effects in cell experiments, indicating its potential in the field of anti-cancer drug development.
2. ** Drugs for neurological diseases **: The incidence of neurological diseases such as Alzheimer's disease and Parkinson's disease is increasing, and there is an urgent need for effective therapeutic drugs. Some nitrogen-containing heterocyclic compounds play an active role in modulating neurotransmitters and protecting nerve cells. 3-Iodo-1H-pyrrolo [2,3-b] pyridine may be able to develop drugs for the treatment of neurological diseases through structural modification, opening up new market space.
###Materials Science Field
1. ** Organic Optoelectronic Materials **: With the development of organic Light Emitting Diode (OLED), organic solar cells and other technologies, the demand for high-performance organic optoelectronic materials has increased sharply. The compound can be used to prepare organic optoelectronic materials due to its conjugated structure or unique photoelectric properties. For example, in OLED display technology, through molecular design and modification, it may be possible to develop luminescent materials with high luminous efficiency and long life to meet the market demand for high-quality display materials.
2. ** Sensor Materials **: In the field of chemical sensors, the demand for high-sensitivity, high-selectivity sensing materials continues to grow. 3-Iodo-1H-pyrrolo [2,3-b] pyridine or because of its special chemical structure, selectively recognizes and responds to specific substances, and then develops sensor materials for detecting environmental pollutants, biomarkers, etc., with broad market application prospects.
However, its market development also faces challenges. The process of synthesizing the compound may be complex and costly, limiting its large-scale production and application. And in the field of pharmaceutical research and development, new drug research and development cycles are long, expensive, and risky. From compound discovery to final drug launch, multiple rounds of clinical trials are required, which is full of uncertainty. But overall, with technological advancements and in-depth research, 3-Iodo-1H-pyrrolo [2,3-b] pyridine is expected to achieve significant development in the pharmaceutical and materials markets if it can overcome difficulties such as synthesis processes.
What are the precautions in the preparation of 3-Iodo-1H-pyrrolo [2,3-b] pyridine?
When preparing 3-iodine-1H-pyrrolido [2,3-b] pyridine, there are several ends that need to be paid attention to.
The selection of starting materials is extremely critical. The purity of the starting material must be excellent. If there are many impurities, the reaction path will be complicated and the product will be impure. And the activity of the starting material also needs to be adapted to the reaction requirements. If the activity is too high, or side reactions will occur. If the activity is too low, the reaction will be slow or even difficult to occur.
The control of the reaction conditions is the most important thing. Temperature must be accurately controlled. If the temperature is too high, the molecular thermal motion intensifies, the probability of side reactions increases greatly, or the product is decomposed; if the temperature is too low, the reaction rate slows down, it takes a long time, or the reaction cannot reach the expected process. For common reactions, every suitable temperature range, such as the preparation of 3-iodine-1H-pyrrolido [2,3-b] pyridine, or a specific temperature range, can make the reaction efficient and the product purity is good.
Furthermore, the reaction solvent also needs to be carefully selected. The solvent not only provides a site for the reaction, but its polarity and solubility properties have a great impact on the reaction process. Polarity-adapted solvents can promote the dissolution and dispersion of the reactants, which is conducive to the reaction; if the solvent is improperly selected, or the reactants are insoluble, the reaction is difficult to occur uniformly, and the product yield and purity are implicated.
During the reaction process, stirring cannot be ignored. Adequate stirring can make the reactants fully contact, mass transfer is uniform, avoid local concentration is too high or too low, reduce side reactions, and improve reaction efficiency and product uniformity. If stirring is insufficient, the reactants are unevenly mixed, the reaction progress is different, and the product quality will be affected.
In the post-processing stage, the operation should also be fine. The steps of product separation and purification are related to the purity of the final product. Appropriate separation methods, such as column chromatography, recrystallization, etc., are selected to remove impurities and obtain high-purity 3-iodine-1H-pyrrolido [2,3-b] pyridine. Improper operation of this process, such as wrong selection of eluent and poor crystallization conditions, will cause product loss or purity substandard.