3-Amino-2-methoxypyridine-5-boronic acid pinacol ester

3-Amino-2-methoxypyridine-5-boronic acid pinacol ester is a crucial compound in the field of organic synthesis. Its chemical properties are unique and contain specific functional groups such as boronic acid pinacol ester and amino, methoxy and pyridine rings.
Boronic acid pinacol ester functional group, with good stability and reactivity. In many organic reactions, such as Suzuki-Miyaura coupling reaction, it can efficiently generate carbon-carbon bonds with halogenated aromatics or halogenated olefins under palladium catalysis, thereby realizing the construction of complex organic molecules, which is widely used in pharmaceutical chemistry, materials science and other fields. As a reactive functional group, the
amino group has nucleophilic properties. It can participate in reactions such as acylation and alkylation, introduce various functional groups to the molecule, or react with other compounds containing active groups to modify and expand the molecular structure. The
methoxy group attached to the pyridine ring will affect the electron cloud density and chemical activity of the pyridine ring. The pyridine ring itself is aromatic and basic. Due to the electron-giving effect of methoxy, the electron cloud density of the pyridine ring increases, which changes its electrophilic substitution activity. Under different reaction conditions, it can exhibit unique reaction selectivity.
In addition, the physical properties of 3-amino-2-methoxypyridine-5-boronic acid pinacol esters, such as solubility, are affected by the functional groups in their structure. It has a certain solubility in organic solvents such as dichloromethane, N, N-dimethylformamide. This property is of great significance for the selection of reaction solvents and the optimization of reaction conditions in organic synthesis operations. When storing and using, it is necessary to pay attention to its stability to air and moisture. Some borate esters may undergo reactions such as hydrolysis in humid air, which affects their quality and reactivity. Therefore, they usually need to be properly stored in a dry and inert gas protected environment.

3-Amino-2-methoxypyridine-5-boronic acid pinacol esters have a wide range of uses and play a significant role in the field of organic synthesis.
First, in the field of medicinal chemistry, it is often a key intermediate. The structure of geinpyridine and borate esters endows compounds with diverse reactivity. By combining with other active groups containing halides and alkenyl groups, complex drug molecular structures can be constructed according to specific reaction mechanisms. For example, the synthesis of some biologically active heterocyclic compounds can participate in the Suzuki-Miyaura coupling reaction and precisely splice different fragments. This reaction condition is mild and highly selective, which can effectively prepare drug precursors with specific pharmacological activities, paving the way for innovative drug research and development.
Second, in the field of materials science, it also has outstanding performance. With its own structural characteristics, materials with special optoelectronic properties can be prepared. For example, in the preparation of organic Light Emitting Diode (OLED) materials, by rational molecular design and modification, it can be introduced into the material skeleton to regulate the material energy level structure and charge transport performance, thereby improving the luminous efficiency and stability of OLED devices. Due to the unique electronic properties of boron atoms, it can affect the material conjugation system and electron cloud distribution, providing the possibility for the creation of new functional materials.
Third, in chemical biology research, it is of great value as a probe molecule building block. Borate esters can specifically bind to biomolecules containing cis-diol structures (such as carbohydrates, nucleosides, etc.). Based on this property, 3-amino-2-methoxypyridine-5-boronic acid pinacol esters are used to construct probes, which can be used for the detection and tracing of carbohydrates and other substances in organisms, helping to reveal relevant physiological and pathological processes in organisms, and contributing to life science research.

The synthesis of 3-amino-2-methoxypyridine-5-boronic acid pinacol esters is an important research topic in the field of organic synthesis. The synthesis path follows the following steps.
First, a suitable pyridine derivative is used as the starting material. If a pyridine compound containing a specific substituent is selected, the substituent must be able to be introduced into the amino group, methoxy group and boric acid pinacol ester group through specific transformation in the subsequent reaction. Usually, pyridine with halogen atom can be selected, and the halogen atom can be chlorine, bromine, etc. Because of its suitable activity, it is convenient to carry out nucleophilic substitution and other reactions. < Br >
Second, the methoxy group is introduced. Nucleophilic substitution reactions often occur with halopyridine as alkoxides. For example, sodium methoxide reacts with halopyridine in a suitable solvent, such as dimethylformamide (DMF), under heating conditions. During this process, the methoxy negative ion of sodium methoxide attacks the carbon atom attached to the halogen atom of halopyridine, and the halogen atom leaves, so the methoxy group is introduced.
Furthermore, the amino group is introduced. This step can be achieved by many methods. One is the reaction of ammonia or ammonia derivatives with methoxy-substituted pyridine. Under high temperature and high pressure conditions, ammonia reacts with pyridine derivatives to achieve the introduction of amino groups. It can also be synthesized by Gabriel method. First, potassium phthalimide is reacted with halopyridine, and then through hydrazinolysis and other steps, the amino substitution product can be obtained.
At the end, the boric acid pinacol ester group is constructed. Often boron-containing reagents, such as diphenyl alcohol borate, and pyridine derivatives of methoxy and amino groups have been introduced, in the presence of a palladium catalyst, such as tetrakis (triphenylphosphine) palladium (0), in an organic solvent, such as toluene, adding an appropriate amount of base, such as potassium carbonate, through a Suzuki-Miyaura coupling reaction process or the like, to achieve the introduction of boronic acid phenyl alcohol ester, and finally obtain 3-amino-2-methoxypyridine-5-boronic acid phenyl alcohol ester. In the
synthesis process, the conditions of each step of the reaction, such as temperature, reaction time, and the proportion of reactants, need to be carefully adjusted to ensure the efficient progress of the reaction and the high purity of the product. The separation and purification steps after each step of the reaction are also crucial, which is related to the quality of the final product.

3-Amino-2-methoxypyridine-5-boronic acid pinacol ester is a commonly used reagent in organic synthesis. When storing, many key matters need to be paid attention to to in order to ensure its quality and activity.
Humidity of the first environment. This compound is quite sensitive to moisture, and moisture invasion can easily cause its hydrolysis and deterioration, and its activity is sharply reduced. Therefore, it should be stored in a dry place, and desiccants can be placed in storage containers, such as anhydrous calcium chloride, silica gel, etc., to remove surrounding moisture and ensure that its environment is dry.
Time and temperature control. In general, it is recommended to store in a low temperature environment to slow down the rate of chemical reactions that may occur and reduce the risk of decomposition. Usually, it can be stored in the refrigerated compartment of the refrigerator, with a temperature of about 2-8 ° C. However, it should be noted that the temperature should not be too low to prevent crystallization or solidification, causing inconvenience in access, or even affecting its structure and properties.
Furthermore, it is necessary to avoid light. Light may trigger photochemical reactions, causing degradation or structural changes of the compound. Therefore, storage containers should have the effect of shading light, such as brown glass bottles, and placed in a dark place, so as not to expose to direct light.
In addition, air isolation should not be ignored. Oxygen in the air or oxidation reaction with the substance will damage its quality. The storage container can be filled with an inert gas, such as nitrogen, to drain the air and form a protective atmosphere.
When using it, it is also necessary to make a quick decision to minimize its exposure to the external environment. After use, seal the container and return it to the original storage conditions. All these are the things that should be paid attention to when storing 3-amino-2-methoxypyridine-5-boronic acid pinacol ester to ensure its stable performance and facilitate subsequent use.

The market price of Wuguanfu 3 - Amino - 2 - methoxypyridine - 5 - boronic acid pinacol ester is difficult to say in a word. Its price often varies due to a variety of reasons.
Let's talk about its raw materials first. The preparation of this compound requires specific starting materials. If the yield of raw materials fluctuates, or the difficulty of obtaining them varies, the price will be affected. If raw materials are scarce, the price will be high; conversely, if raw materials are abundant and easy to obtain, the price may decline.
Furthermore, the preparation process is also key. The delicate and efficient process can reduce costs. However, if the process is complicated and requires many steps and special reagents, the cost will rise and the price will also rise.
The state of supply and demand in the market also affects its price. If at some point, many companies seek to buy this product for use in pharmaceutical research and development, organic synthesis and other fields, the demand is strong but the supply is limited, and the price is high; if the supply exceeds the demand, merchants may sell their products at a reduced price.
There is a difference in quality. High-quality products have few impurities and high purity, and are mostly used for high-end scientific research and production. The price must be higher than that of ordinary quality products.
Looking at the example of "Tiangong Kaiwu" in the past, the prices of the items recorded in it also vary according to the region, season, supply and demand. Today's price of 3-Amino-2-methoxypyridine-5-boronic acid pinacol ester is also similar to this. In the market, it can range from tens of yuan per gram to hundreds of yuan, or even higher. It is difficult to determine an exact number. It must be studied carefully according to the current specific market conditions, quality specifications, etc.