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| | N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide Basic information |
| Product Name: | N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide | | Synonyms: | N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide;N-[4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-
yl]acetaMide;184572;Acetamide, N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]-;(2-acetamidopyridin-4-yl)boronic acid pinacol ester;N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide ISO 9001：2015 REACH;2-acetyl aminopyridine-4-phenool borate | | CAS: | 1220220-21-2 | | MF: | C13H19BN2O3 | | MW: | 262.11 | | EINECS: | 214-589-6 | | Product Categories: | | | Mol File: | 1220220-21-2.mol |  |
| | N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide Chemical Properties |
| Boiling point | 451.8±30.0 °C(Predicted) | | density | 1.11±0.1 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 13.92±0.70(Predicted) | | Appearance | Off-white to gray Solid | | InChI | InChI=1S/C13H19BN2O3/c1-9(17)16-11-8-10(6-7-15-11)14-18-12(2,3)13(4,5)19-14/h6-8H,1-5H3,(H,15,16,17) | | InChIKey | LXSZMGQQXZXQKX-UHFFFAOYSA-N | | SMILES | C(NC1=NC=CC(B2OC(C)(C)C(C)(C)O2)=C1)(=O)C |
| | N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide Usage And Synthesis |
| Synthesis | GENERAL STEPS: To a 1L four-necked flask equipped with a magnetic stirrer, thermometer, reflux condenser and bubbler was added 55.91 g (0.26 mol) of N-(4-bromo-pyridin-2-yl)acetamide and 66.02 g (0.26 mol) of bis(boronic acid) pinacol ester, followed by 76.44 g (0.78 mol) of potassium acetate and 450 mL of dioxane, and mixed by stirring. Under nitrogen protection, 3.81 g (0.0051 mol) of palladium dichlorodichalcogenide was added and the reaction was warmed to 100 °C for 18 to 24 h. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, it was cooled to room temperature, precipitated as a solid, pulped and filtered. The filtrate was dissolved in 500 mL of methanol, filtered again, and the filtrate evaporated to dryness. Finally, heptane was added for pulping to obtain 62.08 g of the target product 2-acetylaminopyridine-4-boronic acid pinacol ester in 91.1% yield. | | References | [1] Patent: CN103601745, 2017, B. Location in patent: Paragraph 0025; 0026
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 36, p. 10890 - 10894
[3] Angew. Chem., 2016, vol. 128, p. 11050 - 11054,5
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5613 - 5637
[5] Patent: US2013/165464, 2013, A1. Location in patent: Paragraph 0835 |
| | N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide Preparation Products And Raw materials |
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