2-METHYLPYRIDINE-4-BORONIC ACID PINACOL ESTER synthesis

4synthesis methods

Product Name:2-METHYLPYRIDINE-4-BORONIC ACID PINACOL ESTER
CAS Number:660867-80-1
Molecular formula:C12H18BNO2
Molecular Weight:219.09

22282-99-1

73183-34-3

2-METHYLPYRIDINE-4-BORONIC ACID PINACOL ESTER

660867-80-1

The general procedure for the synthesis of 2-methyl-4-pyridylboronic acid pinacol ester from 4-bromo-2-methylpyridine (0.500 g, 2.906 mmol) and pinacol ester of bis(diphenylphosphine) (0.812 g, 3.997 mmol) is as follows: in an inert atmosphere, 4-bromo-2-methylpyridine, pinacol ester of bis(boronic acid), potassium acetate (0.854 g, 8.720 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.021 g, 0.029 mmol) were dissolved in degassed 1,4-dioxane (5 mL) in a 50 mL sealed tube. The reaction mixture was stirred at 80 °C for 4 hours. Upon completion of the reaction, the solvent was removed by rotary evaporation and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/ether = 30:70) to afford 2-methyl-4-pyridinylboronic acid pinacol ester (0.250 g, 39% yield) as an off-white solid. m/z 220.1 [M + H]+ was shown by LCMS analysis.

22282-99-1 Synthesis

22282-99-1
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$6.00/5g

73183-34-3
583 suppliers
$6.00/5g

660867-80-1
167 suppliers
$11.00/250mg

Yield: 70%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane at 90; for 12 h;Inert atmosphere;Miyaura Borylation Reaction;

Steps:

4.3. General methods for intermediates 6 and 10
General procedure: To a solution of borate (1 equiv) and bipinacol borate (1.2 equiv)in anhydrous dioxane, KOAc (3 equiv) and Pd(dppf)Cl2 (0.05% mol)were added. After reaction at 90 C for 12 h under N2 atmosphere,the solvent was concentrated and water was added to the reactionflask, and then the filter cake was washed with petroleum etherand acetonitrile to obtain the intermediates 6 and 10.

References:

Chen, Huanhua;Ding, Huaiwei;Gao, Yaping;Jiang, Xiaowen;Liu, Wenjie;Liu, Wenwu;Liu, Xin;Tian, Liting;Xu, Zihua;Zhao, Qingchun [European Journal of Medicinal Chemistry,2021,vol. 222]