| Identification | Back Directory | [Name]
6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole | [CAS]
937049-58-6 | [Synonyms]
Indazole-6-boronic acid pinacolate
Pinacol ester indazole-6-boronic acid
1H-Indazole-6-boronic acid picol ester
Indazole-6-yl-boronic acid pinacol ester
6-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole
6-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-INDAZOLE
1H-Indazole, 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole, 2-(1H-Indazol-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | [Molecular Formula]
C13H17BN2O2 | [MDL Number]
MFCD07368067 | [MOL File]
937049-58-6.mol | [Molecular Weight]
244.1 |
| Chemical Properties | Back Directory | [Melting point ]
134-139°C | [Boiling point ]
404.1±18.0 °C(Predicted) | [density ]
1.15±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,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 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole(937049-58-6)1HNMR
6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole(937049-58-6)FT-IR
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| Hazard Information | Back Directory | [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 |
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