6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole synthesis
- Product Name:6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole
- CAS Number:937049-58-6
- Molecular formula:C13H17BN2O2
- Molecular Weight:244.1
79762-54-2
73183-34-3
937049-58-6
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.
79762-54-2
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73183-34-3
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937049-58-6
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Yield: 100%
Reaction Conditions:
with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;potassium acetate in N,N-dimethyl-formamide at 100; for 15 h;Inert atmosphere;
Steps:
I.1.3 6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-indazole
A mixture of 6-bromo-1 /-/-indazole (700 mg; 3.55 mmol), 4,4,4',4',5,5,5',5'-octamethyl- 2,2'-bi(1 ,3,2-dioxaborolane) (1 .50 g; 5.91 mmol), Pd(dppf)CI2- DCM (290 mg; 0.36 mmol) and KOAc (1 .04 g; 10.6 mmol) in DMF (20 mL) was stirred at 100°C for 15 hours under nitrogen. The mixture was concentrated in vacuo, suspended in EtOAc (30 mL), filtered through Celite, and concentrated to afford 866 mg (100%) of the title compound as a brown semi-solid, which was used directly without further purification. LC-MS for Ci3H17BN2O2+H+ [M+H]+: calcd. 245.1 ; found: 245.0.
References:
ITEOS THERAPEUTICS;CAUWENBERGHS, Sandra;CROSIGNANI, Stefano;DRIESSENS, Gregory;DEROOSE, Frederik WO2015/140717, 2015, A1 Location in patent:Page/Page column 87; 88
39478-78-9
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937049-58-6
136 suppliers
$22.00/100mg