4-Pyrazoleboronic Acid Pinacol Ester For Baricitinib CAS 269410-08-4

Basic Info

Model No.: 269410-08-4

Grade Standard: Medicine Grade

State: Solid

Additional Info

Packaging: 25KGS/DRUM

Productivity: Custom Manufacturing

Brand: VOLSENCHEM

Transportation: Air

Place of Origin: CHINA

Supply Ability: In stock

Product Description

Baricitinib intermediate called 4-Pyrazoleboronic acid pinacol ester CAS number is 269410-08-4, his preparation methods are mainly the following two methods. One is use 1-methylpyrazole and isopropanol pinacol boron acid ester as a starting material, reacted with n-butyllithium at -78℃, quenched, washed with water, extracted with dichloromethane, and concentrated to give a crude 4-Pyrazoleboronic acid pinacol ester. This synthetic route is not suitable for industrial scale mass production because the extracted dichloromethane solution is directly concentrated to dryness to obtain a crude product, which is difficult to achieve in an actual production.
Method 2: using 1-methylpyrazole and pinacol borane as starting materials, reacting at normal temperature, washing with pentane, and concentrating to obtain crude 4-pyrazoleboronic acid pinacol ester. This synthetic route is also not suitable for industrial mass production because the raw material pinacol borane is relatively expensive and costly. The extracted pentane solution is directly concentrated to dryness to obtain a crude product, which is difficult to handle in industrial production. The main drawback of the above two processes is that post-processing is not easy to amplify. Therefore, it is particularly important to find a method that can be applied to production on a large scale.
    There is a technical solution that we think is more feasible. The specific process is as follows: 1. Add 1-methyl-4-pyrazolecarboxylic acid and anhydrous tetrahydrofuran to the reaction flask, and cool the solution to -60℃- 70℃, slowly add dropwise 1.1~1.2 equivalents of n-butyl lithium, control the dropping temperature not exceeding -60℃, react at -60℃ - 70℃ for 2 ~ 3 h, then slowly add triisopropyl borate, continue at -60℃ - 70℃ reaction for 2~3h, then increase to room temperature for 8~12h, after the reaction is finished, cool down to 0~10°C, quench the reaction solution with saturated ammonium chloride solution, adjust the pH to 5~6 with 2N hydrochloric acid solution, and let stand. Layered. The aqueous layer was extracted three times with ethyl acetate. The organic layer was concentrated, and then evaporated, and then evaporated and evaporated. Filtration, the filter cake was rinsed with n-heptane and dried to give the first compound. 2. Add the first step compound, pinacol and anhydrous tetrahydrofuran to the reaction flask in turn, stir at room temperature until the solid dissolves, then add anhydrous magnesium sulfate, react at room temperature for 8~12h, filter after reaction, and use 10 times mother liquor. The volume is washed twice, the organic layer is concentrated to 1 to 2 times the volume, the solution is cooled to -10 to 0℃, and stirred for 4 to 6 hours. Filtration and drying gave the desired product 4-Pyrazoleboronic acid pinacol ester CAS number 269410-08-4.

Thera Category: JAK Inhibitor

Cas No.:  269410-08-4 

Synonym: PYRAZOLE-4-BORONIC ACID PINACOL ESTER;1H-PYRAZOLE-4-BORONIC ACID PINACOL ESTER;4-PYRAZOLEBORONIC ACID PINACOL ESTER;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE;4,4,5,5-TETRAMETHYL-2-(1H-PYRAZOL-4-YL)-1,3,2-DIOXABOROLANE;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 97+%;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole,min.97%;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, min. 97%

Molecular Formula: C9H15BN2O2

Molecular Weight:  194.04

Specifications: Available on request

Packing:Export worthy packing

Material Safety Data Sheet:Available on request

Related intermediates:

1) Pyrazole-4-Boronic Acid Pinacol Ester CAS 269410-08-4
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