| Identification | Back Directory | [Name]
2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridin-3-ylamine | [CAS]
893440-50-1 | [Synonyms]
3-Amino-2-methoxypyridin-5-ylboronic acid
2-Methoxy-3-aminopyridine-5-boronic acid pinacol ester
5-Amino-6-methoxypyridine-3-boronic acid pinacol ester
3-Amino-2-methoxypyridine-5-boronicacidpinacolester,96%
(5-amino-6-methoxypyridin-3-yl)boronic acid pinacol ester
2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
3-AMino-2-Methoxypyridine-5-boronic acid pinacol ester, 96%
2-Methoxy-5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-aMine
2-(5-Amino-6-methoxy-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-aMine
2-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-aMine
2-Methoxy-3-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
3-Amino-2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2-dioxaborolan-2-yl)pyridine
3-Pyridinamine, 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
2-(Methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]
dioxaborolan-2-yl)-pyridin-3-ylamine
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 | [Molecular Formula]
C12H19BN2O3 | [MDL Number]
MFCD12923427 | [MOL File]
893440-50-1.mol | [Molecular Weight]
250.104 |
| Chemical Properties | Back Directory | [Melting point ]
131-133℃ | [Boiling point ]
392.3±42.0 °C(Predicted) | [density ]
1.11±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,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 |
| Hazard Information | Back Directory | [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 |
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