2-METHOXYPYRIDINE-5-BORONIC ACID PINACOL ESTER Chemical Properties

Melting point:

47-51 °C(lit.)

Boiling point:

102°C/0.08mmHg(lit.)

Density 

1.06±0.1 g/cm3(Predicted)

Flash point:

216 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Soluble in water

form 

powder to crystal

pka

3.39±0.12(Predicted)

color 

White to Almost white

CAS DataBase Reference

445264-61-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2933399990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-METHOXYPYRIDINE-5-BORONIC ACID PINACOL ESTER Usage And Synthesis

Uses

(2-Methoxypyridin-5-yl)boronic Acid Pinacol Ester is used in the design and synthesis of oxazolidinone antibacterial agents. As well, it is used in the synthesis of [3,2-b]pyridines.

Uses

2-Methoxypyridine-5-boronic acid pinacol ester is used in the design and synthesis of oxazolidinone antibacterial agents. As well, it is used in the synthesis of [3,2-b]pyridines.

Synthesis

Step 1: 5-bromo-2-methoxypyridine (55 g, 0.29 mol), pinacol ester of bisboronic acid (90 g, 0.35 mol), potassium acetate (57 g, 0.58 mol) and bis(triphenylphosphine)palladium(II) chloride (2.2 g, 3 mmol) were dissolved in anhydrous dioxane (500 mL) under nitrogen protection. The reaction mixture was heated and stirred at 108 °C overnight. Upon completion of the reaction, the mixture was concentrated and purified by column chromatography using hexane/ethyl acetate as eluent to afford pinacol ester of 6-methoxypyridine-3-boronic acid (58 g, 84% yield).

References

[1] Patent: US9249156, 2016, B2. Location in patent: Page/Page column 36
[2] Patent: WO2018/85342, 2018, A1. Location in patent: Page/Page column 26; 28
[3] Patent: WO2014/186035, 2014, A1. Location in patent: Page/Page column 151
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2496 - 2500
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6477 - 6485

2-METHOXYPYRIDINE-5-BORONIC ACID PINACOL ESTER(445264-61-9)Related Product Information

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• p-Anisaldehyde
• 4-Methoxybenzylchloride
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• 3-(METHOXYMETHOXY)BENZALDEHYDE
• (Trifluoromethoxy)benzene
• Bis(pinacolato)diboron
• Tris(trimethylsilyl)phosphate
• Dimethyl succinate
• EPA
• Anisole
• Methyl acrylate
• 4-Methoxyphenylacetone
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• 2-ISOPROPOXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 2-BENZYLOXYPYRIDINE-5-BORONIC ACID, PINACOL ESTER
• 2-(CYCLOPROPYLMETHOXY)-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 2-ETHOXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE