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| | 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Basic information |
| Product Name: | 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | | Synonyms: | 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1H-Pyrazole, 1-(1-ethoxyethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;1-(1-ethoxyethyl)-4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)boronic acid;1-(1-ethoxyethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyrazole;1-(1-Ethoxyethyl)-1H-pyrazole-4-boronic acid pinacol ester;1-(1-EthoxyEthyl)-Pyrazole- 4-Boronic acid Pinacolate;1-(1-Ethoxyethyl) | | CAS: | 1029716-44-6 | | MF: | C13H23BN2O3 | | MW: | 266.14 | | EINECS: | 689-230-6 | | Product Categories: | 1029716-44-6 | | Mol File: | 1029716-44-6.mol |  |
| | 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Chemical Properties |
| Boiling point | 353.3±22.0 °C(Predicted) | | density | 1.06 | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 1.55±0.10(Predicted) | | form | solid | | color | White | | InChI | InChI=1S/C13H23BN2O3/c1-7-17-10(2)16-9-11(8-15-16)14-18-12(3,4)13(5,6)19-14/h8-10H,7H2,1-6H3 | | InChIKey | IZKVGEWCELXYRI-UHFFFAOYSA-N | | SMILES | N1(C(OCC)C)C=C(B2OC(C)(C)C(C)(C)O2)C=N1 |
| Hazard Codes | Xn | | Risk Statements | 22 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 2933199090 |
| | 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Usage And Synthesis |
| Uses | 1-(1-Ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is an important pharmaceutical intermediate of Baricitinib.
| | Synthesis | Step 3: To a pre-oven-dried vial at room temperature was added a lithium isopropylmagnesium chloride solution (1.0 M, dissolved in THF, 6.32 mL, 8.22 mmol). Subsequently, 4-bromo-1-(1-ethoxyethyl)-1H-pyrazole (1.00 g, 4.56 mmol) was slowly added dropwise to this solution. The reaction mixture was stirred continuously at room temperature for 16 hours. Upon completion of the reaction, the mixture was cooled to -20 °C and 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.73 g, 10.95 mmol) was added via syringe. Subsequently, the reaction mixture was slowly warmed up to room temperature. After continued stirring at room temperature for 2 h, the reaction was quenched by the addition of saturated aqueous ammonium chloride solution (15 mL), at which time the formation of a white precipitate was observed. The mixture was diluted with additional water (20 mL) and extracted with hexane (140 mL each time, 2 times). The organic phases were combined and washed sequentially with saturated aqueous sodium bicarbonate and brine, then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to give 1.20 g (99% yield) of the target product 1-(1-ethoxyethyl)-4-pyrazoleboronic acid pinacol ester as a colorless oil. | | References | [1] Patent: WO2014/74661, 2014, A1. Location in patent: Paragraph 00251
[2] Patent: WO2015/69310, 2015, A1. Location in patent: Paragraph 00175
[3] Patent: TWI582077, 2017, B. Location in patent: Page/Page column 82
[4] Organic Letters, 2009, vol. 11, # 9, p. 1999 - 2002
[5] Patent: US2010/190981, 2010, A1. Location in patent: Page/Page column 105 |
| | 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Preparation Products And Raw materials |
| Raw materials | 1H-Pyrazole, 4-broMo-1-(1-ethoxyethyl)--->4-Pyrazoleboronic acid pinacol ester-->2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-->1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole-->Ethyl vinyl ether-->Bis(pinacolato)diboron-->Tetrahydrofuran-->Lithium chloride-->ISOPROPYLMAGNESIUM CHLORIDE-->2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
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