6-Dimethylaminopyridine-3-boronic acid pinacol ester Chemical Properties

Melting point:

89-90 °C

Boiling point:

358.5±27.0 °C(Predicted)

Density 

1.04±0.1 g/cm3(Predicted)

storage temp. 

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

pka

6.98±0.10(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

HS Code 

2933399990

6-Dimethylaminopyridine-3-boronic acid pinacol ester Usage And Synthesis

Uses

6-(Dimethylamino)pyridine-3-boronic acid pinacol ester

Synthesis

General procedure for the synthesis of N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine from 5-bromo-N,N-dimethylpyridin-2-amine and pinacol bis(boronic acid) ester: Under nitrogen protection, potassium acetate (8.3 g, 42.3 mmol) and [1,1,7 mmol] were added to a solution of 5-bromo-N,N-dimethylpyridin-2-amine (8.5 g, 42.3 mmol) and pinacol bis(boronic acid) ester (12.9 g, 50.7 mmol) to a solution of dioxane (10 mL) was added potassium acetate (8.3 g, 84.6 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1.55 g, 2.1 mmol). The reaction mixture was stirred at 25°C and subsequently heated to 100°C and kept for 12 hours. The completion of the reaction was monitored by LCMS. After completion of the reaction, the mixture was filtered and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 50/1 to 3/1) to afford the target compound 2-(2-(N,N-dimethylamino)pyridin-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes (8 g, 32.2 mmol, 76% yield) as yellow solid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.53 (s, 1H), 7.75-7.78 (d, 1H), 6.43-6.45 (d, 1H), 3.09 (s, 6H), 1.22-1.30 (m, 12H).ESI-MS (m/z): 249.2 [M+H]+.

References

[1] Patent: WO2017/120429, 2017, A1. Location in patent: Page/Page column 262
[2] Advanced Synthesis and Catalysis, 2010, vol. 352, # 11-12, p. 2002 - 2010
[3] European Journal of Organic Chemistry, 2012, # 3, p. 595 - 603
[4] Patent: WO2017/98440, 2017, A1. Location in patent: Page/Page column 248

6-Dimethylaminopyridine-3-boronic acid pinacol ester(1036991-24-8)Related Product Information

• 2-METHYLSULFANYL-5-(4,4,5,5-TETRAMETHYL-[1,3,2]-DIOXABOROLAN-2-YL)PYRIDINE
• 6-(4-MORPHOLINEAMINO)PYRIDINE-3-BORONIC ACID PINACOL ESTER
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• TERT-BUTYL N-METHYL-N-[3-METHYL-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDIN-2-YL]CARBAMATE
• 2-(CYCLOPROPYLMETHOXY)-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE-2-CARBOXYLIC ACID DIETHYLAMIDE
• 2-Dimethylamino-pyrimidine-5-boronic acid pinacol ester