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| | 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridin-3-ylamine Basic information |
| Product Name: | 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridin-3-ylamine | | Synonyms: | 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridin-3-ylamine;5-Amino-6-methoxypyridine-3-boronic acid pinacol ester;2-Methoxy-5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-aMine;3-AMino-2-Methoxypyridine-5-boronic acid pinacol ester, 96%;2-Methoxy-3-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine, 2-(5-Amino-6-methoxypyridin-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(Methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine;-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-aMine | | CAS: | 893440-50-1 | | MF: | C12H19BN2O3 | | MW: | 250.1 | | EINECS: | | | Product Categories: | | | Mol File: | 893440-50-1.mol | ![2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridin-3-ylamine Structure](CAS/GIF/893440-50-1.gif) |
| | 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridin-3-ylamine Chemical Properties |
| Melting point | 131-133℃ | | Boiling point | 392.3±42.0 °C(Predicted) | | density | 1.11±0.1 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | form | powder to crystal | | pka | 4.32±0.22(Predicted) | | color | White to Gray to Brown | | Water Solubility | Slightly soluble in water. | | InChI | InChI=1S/C12H19BN2O3/c1-11(2)12(3,4)18-13(17-11)8-6-9(14)10(16-5)15-7-8/h6-7H,14H2,1-5H3 | | InChIKey | KYYKGOURQXPERA-UHFFFAOYSA-N | | SMILES | C1(OC)=NC=C(B2OC(C)(C)C(C)(C)O2)C=C1N |
| | 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridin-3-ylamine Usage And Synthesis |
| Uses | It is used as a pharmaceutical intermediate. | | Synthesis | Step A: Synthesis of 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine
[00403] Degassed 5-bromo-2-methoxypyridin-3-amine (2 g, 9.85 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl pinacol ester (3.00 g, 11.82 mmol), Pd(dppf)2Cl2-CH2Cl2 adduct (0.804 g, 0.985 mmol) and potassium acetate (3.87 g, 39.4 mmol) in 1,4-dioxane (50 mL) was heated at 100 °C for 18 h followed by stirring at room temperature overnight. Upon completion of the reaction, the mixture was filtered through a Celite pad and washed with EtOAc. The filtrate was concentrated and the residual solvent was removed by azeotropy with CH2Cl2/hexane. The crude product was dissolved in CH2Cl2 and purified by silica gel column chromatography (elution gradient: 0-100% EtOAc/hexane) to afford 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (3.9 g, 9.36 mmol, 95% yield) as a light brown solid.1H NMR (400 MHz, DMSO-d6) was performed on a 1H NMR pad. MHz, DMSO-d6) δ ppm: 1.26 (s, 12H), 3.87 (s, 3H), 4.92 (s, 2H), 7.12 (d, J = 1.46 Hz, 1H), 7.63 (d, J = 1.37 Hz, 1H); ES LC-MS m/z = 251.4 (M + H)+. | | References | [1] Patent: WO2012/174312, 2012, A2. Location in patent: Page/Page column 287
[2] Patent: WO2014/6554, 2014, A1. Location in patent: Page/Page column 43
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 2091 - 2106
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7381 - 7399
[5] Patent: WO2014/60431, 2014, A1. Location in patent: Page/Page column 85 |
| | 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridin-3-ylamine Preparation Products And Raw materials |
| Raw materials | benzyl 2-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbaMate-->5-Bromo-2-methoxy-3-cyanopyridine-->2-Methoxy-3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridine-->Bis(pinacolato)diboron-->1,4-Dioxane-->Potassium Acetate | | Preparation Products | 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide |
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