1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Chemical Properties

Boiling point:

353.3±22.0 °C(Predicted)

Density 

1.06

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

1.55±0.10(Predicted)

form 

solid

color 

White

InChI

InChI=1S/C13H23BN2O3/c1-7-17-10(2)16-9-11(8-15-16)14-18-12(3,4)13(5,6)19-14/h8-10H,7H2,1-6H3

InChIKey

IZKVGEWCELXYRI-UHFFFAOYSA-N

SMILES

N1(C(OCC)C)C=C(B2OC(C)(C)C(C)(C)O2)C=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933199090

1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Usage And Synthesis

Uses

1-(1-Ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is an important pharmaceutical intermediate of Baricitinib.

Synthesis

Step 3: To a pre-oven-dried vial at room temperature was added a lithium isopropylmagnesium chloride solution (1.0 M, dissolved in THF, 6.32 mL, 8.22 mmol). Subsequently, 4-bromo-1-(1-ethoxyethyl)-1H-pyrazole (1.00 g, 4.56 mmol) was slowly added dropwise to this solution. The reaction mixture was stirred continuously at room temperature for 16 hours. Upon completion of the reaction, the mixture was cooled to -20 °C and 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.73 g, 10.95 mmol) was added via syringe. Subsequently, the reaction mixture was slowly warmed up to room temperature. After continued stirring at room temperature for 2 h, the reaction was quenched by the addition of saturated aqueous ammonium chloride solution (15 mL), at which time the formation of a white precipitate was observed. The mixture was diluted with additional water (20 mL) and extracted with hexane (140 mL each time, 2 times). The organic phases were combined and washed sequentially with saturated aqueous sodium bicarbonate and brine, then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to give 1.20 g (99% yield) of the target product 1-(1-ethoxyethyl)-4-pyrazoleboronic acid pinacol ester as a colorless oil.

References

[1] Patent: WO2014/74661, 2014, A1. Location in patent: Paragraph 00251
[2] Patent: WO2015/69310, 2015, A1. Location in patent: Paragraph 00175
[3] Patent: TWI582077, 2017, B. Location in patent: Page/Page column 82
[4] Organic Letters, 2009, vol. 11, # 9, p. 1999 - 2002
[5] Patent: US2010/190981, 2010, A1. Location in patent: Page/Page column 105

1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(1029716-44-6)Related Product Information

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