2-METHYLPYRIDINE-4-BORONIC ACID PINACOL ESTER Chemical Properties

Melting point:

66-71°C

Boiling point:

315.9±30.0 °C(Predicted)

Density 

1.02

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

5.11±0.10(Predicted)

color 

White to Almost white

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

HS Code 

2933399990

2-METHYLPYRIDINE-4-BORONIC ACID PINACOL ESTER Usage And Synthesis

Synthesis

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.

References

[1] Patent: WO2014/111871, 2014, A1. Location in patent: Page/Page column 199
[2] Patent: WO2004/14913, 2004, A2. Location in patent: Page 82
[3] Patent: US2011/190269, 2011, A1. Location in patent: Page/Page column 36
[4] Patent: WO2011/92272, 2011, A1. Location in patent: Page/Page column 73
[5] Patent: WO2011/119518, 2011, A1. Location in patent: Page/Page column 47-48

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