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| | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole Basic information |
| Product Name: | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole | | Synonyms: | 1-([2-(Trimethylsilyl)ethoxy]methyl)-1H-pyrazole-4-boronic acid pinacol ester;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole;trimethyl-[2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]methoxy]ethyl]silane;1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazole-4-boronic acid picol ester;Baricitinib Impurity 26;4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole;baricitini;1H-Pyrazole, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]- | | CAS: | 894807-98-8 | | MF: | C15H29BN2O3Si | | MW: | 324.3 | | EINECS: | | | Product Categories: | | | Mol File: | 894807-98-8.mol | ![4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole Structure](CAS/20180713/GIF/894807-98-8.gif) |
| | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole Chemical Properties |
| Boiling point | 395.1±27.0 °C(Predicted) | | density | 1.01 | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 1.52±0.10(Predicted) | | Appearance | Colorless to off-white Liquid | | InChI | InChI=1S/C15H29BN2O3Si/c1-14(2)15(3,4)21-16(20-14)13-10-17-18(11-13)12-19-8-9-22(5,6)7/h10-11H,8-9,12H2,1-7H3 | | InChIKey | FERKWUXUTFCIFW-UHFFFAOYSA-N | | SMILES | N1(COCC[Si](C)(C)C)C=C(B2OC(C)(C)C(C)(C)O2)C=N1 |
| | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole Usage And Synthesis |
| Synthesis | General procedure: 1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole-4-boronic acid pinacol ester was synthesized from 4-pyrazoleboronic acid pinacol ester and 2-(trimethylsilyl)ethoxymethyl chloride. To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (8.2 g, 41 mmol) in N-methylpyrrolidone (NMP, 60 mL) was added sequentially potassium carbonate (K2CO3, 12 g, 82 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (7.8 mL, 43 mmol). The reaction mixture was stirred at room temperature for 16 h under the protection of nitrogen (N2). After completion of the reaction, the mixture was diluted and filtered and the filtrate was diluted with ethyl acetate (EtOAc, 300 mL). The resulting solution was washed sequentially with saturated sodium bicarbonate (NaHCO3) aqueous solution (3×200 mL), water (4×200 mL) and brine (1×200 mL), dried over anhydrous sodium sulfate (Na2SO4), filtered, concentrated and dried in vacuum to afford the intermediate 1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole-4-boronic acid pinacol ester ( 11.4 g, yield 86%) as a light yellow oil. | | References | [1] Patent: WO2011/149874, 2011, A2. Location in patent: Page/Page column 81-82
[2] Patent: WO2016/25918, 2016, A1. Location in patent: Paragraph 96-98
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 10, p. 3075 - 3080
[4] Patent: WO2015/95767, 2015, A1. Location in patent: Page/Page column 325
[5] Patent: WO2013/131609, 2013, A1. Location in patent: Page/Page column 112 |
| | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole Preparation Products And Raw materials |
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