6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole Chemical Properties

Melting point:

134-139°C

Boiling point:

404.1±18.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

13.78±0.40(Predicted)

color 

White

InChI

InChI=1S/C13H17BN2O2/c1-12(2)13(3,4)18-14(17-12)10-6-5-9-8-15-16-11(9)7-10/h5-8H,1-4H3,(H,15,16)

InChIKey

YDWZPHAJTNZBEG-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(B3OC(C)(C)C(C)(C)O3)=C2)C=N1

Safety Information

WGK Germany 

3

HS Code 

2933998090

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole Usage And Synthesis

Synthesis

6-Bromo-1H-indazole (700 mg, 3.55 mmol) and pinacol ester of bisboronic acid (1.50 g, 5.91 mmol) were used as raw materials, and both were mixed with Pd(dppf)Cl2-DCM (290 mg, 0.36 mmol) and KOAc (1.04 g, 10.6 mmol) in DMF (20 mL) under nitrogen protection. . The reaction mixture was stirred at 100 °C for 15 hours. Upon completion of the reaction, the mixture was concentrated in vacuum and the residue was suspended in EtOAc (30 mL), filtered through diatomaceous earth, and the filtrate was concentrated to give 866 mg (100% yield) of 1H-indazole-6-boronic acid pinacol ester as a brown semi-solid, which could be used for the subsequent reaction without further purification.Results of LC-MS analysis: C13H17BN2O2 + H+ [M + H]+ , calculated value 245.1, measured value 245.0.

References

[1] Patent: WO2015/140717, 2015, A1. Location in patent: Page/Page column 87; 88
[2] Patent: WO2017/68064, 2017, A1. Location in patent: Page/Page column 182
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 10, p. 4458 - 4473
[4] Patent: US2007/203143, 2007, A1. Location in patent: Page/Page column 50
[5] RSC Advances, 2017, vol. 7, # 44, p. 27737 - 27746

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole(937049-58-6)Related Product Information

• 7-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-INDAZOLE