3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE Chemical Properties

Melting point:

63.4-63.8°C

Boiling point:

341.4±27.0 °C(Predicted)

Density 

1.34

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

2.86±0.22(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE Usage And Synthesis

Synthesis

Preparation of compound 4-1 (5-bromopyridine-3-boronic acid pinacol ester) [221]: In a dry reaction flask 3,5-dibromopyridine (25 g, 105.5 mmol), pinacol ester of biboronic acid (28 g, 110.8 mmol), PdCl2(PPh3)2 (3.7 g, 5.27 mmol), and KOAc (20.7 g 211 mmol), and then 1,4-dioxane (211 mL) was added. The reaction mixture was stirred at reflux for 2 h at 120 °C. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated. The crude product was purified by column chromatography to afford compound 4-1 (25 g, 86% yield) as a white solid.

References

[1] Patent: WO2016/186321, 2016, A1. Location in patent: Paragraph 220-221

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