2-METHOXYLYPYRIDINE-4-BORONIC ACID PINACOLATE Chemical Properties

Melting point:

36 °C

Boiling point:

329.1±27.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to lump

pka

2.56±0.10(Predicted)

color 

White to Almost white

Safety Information

HS Code 

2933399990

2-METHOXYLYPYRIDINE-4-BORONIC ACID PINACOLATE Usage And Synthesis

Synthesis

A mixture of 4-iodo-2-methoxypyridine (0.099 g, 0.42 mmol), pinacol ester of bis(boronic acid) (0.12 g, 0.47 mmol), and potassium acetate (0.13 g, 1.31 mmol) was added to a microwave reactor containing dimethylformamide (1 mL) protected by nitrogen and nitrogen was bubbled for 5 min. Subsequently, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride complex with dichloromethane (1:1) (0.017 g, 0.02 mmol) was added, and the reactor was sealed, and microwave irradiation was carried out for 4 hr at 80 °C. After completion of the reaction, the mixture was diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate was washed sequentially with saturated aqueous sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate and concentrated to give 2-methoxypyridine-4-boronic acid pinacol ester (0.28 g, 82% yield) as a brown oil, which can be used directly in the next step of the reaction.LRMS (m/z): 236 (M + 1).

References

[1] Patent: WO2011/76419, 2011, A1. Location in patent: Page/Page column 131
[2] Patent: EP2338888, 2011, A1. Location in patent: Paragraph 0213; 0214

2-METHOXYLYPYRIDINE-4-BORONIC ACID PINACOLATE(408502-23-8)Related Product Information

• 3-CHLORO-2-METHOXY-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE
• 3-FORMYL-2-METHOXYPYRIDINE-4-BORONIC ACID PINACOL ESTER
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• 5-FLUORO-2-METHOXYPYRIDINE-4-BORONIC ACID PINACOL ESTER
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