5-Trifluoromethylpyridine-3-boronic acid pinacol ester Chemical Properties

Boiling point:

313.6±42.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

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

pka

2.80±0.22(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C12H15BF3NO2/c1-10(2)11(3,4)19-13(18-10)9-5-8(6-17-7-9)12(14,15)16/h5-7H,1-4H3

InChIKey

LFZDWNHGQKQVIG-UHFFFAOYSA-N

SMILES

C1=NC=C(C(F)(F)F)C=C1B1OC(C)(C)C(C)(C)O1

Safety Information

HS Code 

2933399990

5-Trifluoromethylpyridine-3-boronic acid pinacol ester Usage And Synthesis

Application

5-Trifluoromethylpyridine-3-boronic acid pinacol ester can be used as an organic synthesis intermediate and a pharmaceutical intermediate, mainly in laboratory research and development and chemical production processes.

Synthesis

The general procedure for the synthesis of 5-trifluoromethylpyridine-3-boronic acid pinacol ester from pinacol ester of biphenylboronic acid and 3-bromo-5-(trifluoromethyl)pyridine was as follows: 3.50 g (15.50 mmol) of 3-bromo-5-(trifluoromethyl)pyridine, 0.54 g (0.8 mmol) of bis(triphenylphosphine)palladium(II) chloride and 4.55 g (46.5 mmol) of potassium acetate were suspended in 75 mL of dioxane and stirred for 15 minutes. Subsequently, 6.42 g (24.8 mmol) of pinacol ester of bisboronic acid (4,4,5,5,4',4',5',5'-octamethyl-[2,2']bis[[1,3,2]dioxaborolane]) was added and the mixture was heated to 100 °C for 20 hours of reaction. Upon completion of the reaction, the mixture was poured into crushed ice, the pH was adjusted to 9-10 with sodium carbonate solution, and then extracted three times with ethyl acetate. The organic phases were combined, washed with water, dried over magnesium sulfate, filtered and concentrated. The residue was purified by fast column chromatography (dichloromethane/methanol, 1:0 to 9:1) to give 3.48 g (82% yield) of 5-trifluoromethylpyridine-3-boronic acid pinacol ester as a colorless solid. Mass spectrum (MS): 273.1 (M+).

References

[1] Patent: US2009/48238, 2009, A1. Location in patent: Page/Page column 20
[2] Patent: WO2013/43521, 2013, A1. Location in patent: Page/Page column 38; 39
[3] Patent: EP2719697, 2014, A1. Location in patent: Paragraph 0210-0212
[4] Patent: EP2891656, 2015, A1. Location in patent: Paragraph 0266

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