1-Cyclopropyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Chemical Properties

Boiling point:

354.3±15.0 °C(Predicted)

Density 

1.16±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.33±0.12(Predicted)

form 

Solid

Appearance

White to off-white Solid

InChI

InChI=1S/C12H19BN2O2/c1-11(2)12(3,4)17-13(16-11)9-7-14-15(8-9)10-5-6-10/h7-8,10H,5-6H2,1-4H3

InChIKey

NLWYVKHISUTBMY-UHFFFAOYSA-N

SMILES

N1(C2CC2)C=C(B2OC(C)(C)C(C)(C)O2)C=N1

Safety Information

WGK Germany 

3

HS Code 

2933199090

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

Chemical Properties

Type of white solid

Uses

1-Cyclopropyl-4-(pinacolylboronate)-pyrazole is a triazolopyridazine compound with the potential to be used in the treatment of cancer, acting as an c-Met kinase inhibitor.

Synthesis

Step 2: In a dry flask, 1-cyclopropyl-4-iodo-1H-pyrazole (405 mg, 1.73 mmol) was dissolved in anhydrous THF (8.0 mL) and the solution was cooled to 0 °C. Under nitrogen protection, isopropylmagnesium chloride solution (2.0 M in THF, 1.04 mL, 2.08 mmol) was slowly added dropwise, keeping the reaction temperature at 0 °C. After the dropwise addition, the reaction mixture was stirred at 0 °C for 45 min. Subsequently, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.53 mL, 2.60 mmol) was added and the reaction mixture was allowed to warm up slowly to room temperature over 1 hour. Upon completion of the reaction, the reaction was quenched with 50% saturated aqueous NH4Cl and extracted with EtOAc. The organic phases were combined, washed with saturated aqueous NaCl, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 20-50% EtOAc/heptane) to afford 405 mg (83% yield) of 1-cyclopropyl-1H-pyrazole-4-boronic acid pinacol ester as a colorless viscous oil.

References

[1] Patent: US2011/230462, 2011, A1. Location in patent: Page/Page column 84

1-Cyclopropyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(1151802-22-0)Related Product Information

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