TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE Chemical Properties

Melting point:

110 °C

Boiling point:

461.4±37.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

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

pka

-1.48±0.30(Predicted)

form 

solid

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

HS Code 

2933998090

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE Usage And Synthesis

Synthesis

Tert-butyl 5-bromo-1H-indazole-1-carboxylate (10.1 mmol) and pinacol ester of bisboronic acid (11.1 mmol) were used as raw materials for the reaction catalyzed by palladium(II) acetate (1.01 mmol) and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (1.01 mmol) with the addition of potassium acetate (30.3 mmol) in triethylamine ( 1.5 mL) solution of potassium acetate (30.3 mmol) and 1,4-dioxane (60 mL) as a solvent, and the reaction was carried out at 110 °C overnight. After completion of the reaction, the mixture was concentrated under reduced pressure and the residue was purified by fast column chromatography (eluent: 5% ethyl acetate/petroleum ether) to afford the target product 1-tert-butoxycarbonylindazole-5-boronic acid pinacol ester as a yellow solid in 74% yield.

References

[1] Patent: WO2011/66211, 2011, A1. Location in patent: Page/Page column 69-70
[2] Organic Letters, 2009, vol. 11, # 13, p. 2860 - 2863
[3] Patent: WO2010/59943, 2010, A2. Location in patent: Page/Page column 83; 84
[4] Patent: WO2006/86705, 2006, A1. Location in patent: Page/Page column 89
[5] Patent: US2008/153813, 2008, A1. Location in patent: Page/Page column 22

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE(864771-44-8)Related Product Information

• TERT-BUTYL FORMATE
• INDAZOLE-5-BORONIC ACID PINACOL ESTER
• 1H-INDAZOLE-5-BORONIC ACID
• 1-METHYLINDAZOL-5-BORONIC ACID
• TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE