| Identification | Back Directory | [Name]
N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide | [CAS]
1220220-21-2 | [Synonyms]
184572
(2-acetamidopyridin-4-yl)boronic acid pinacol ester
N-[4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-
yl]acetaMide
N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide
Acetamide, N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]-
N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide ISO 9001：2015 REACH | [EINECS(EC#)]
214-589-6 | [Molecular Formula]
C13H19BN2O3 | [MDL Number]
MFCD11878181 | [MOL File]
1220220-21-2.mol | [Molecular Weight]
262.11 |
| Chemical Properties | Back Directory | [Boiling point ]
451.8±30.0 °C(Predicted) | [density ]
1.11±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,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 |
| Hazard Information | Back Directory | [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 |
|
|