| Company Name: |
Energy Chemical |
| Tel: |
400-0056266 |
| Email: |
sales8178@energy-chemical.com |
|
| | 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one Basic information |
| Product Name: | 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one | | Synonyms: | Oxindole-6-boronic acid, pinacol ester;2-Oxoindoline-6-boronic Acid Pinacol Ester;6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indol-2-one;6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one;6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one;2H-Indol-2-one, 1,3-dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;Oxindole-6-boronic;6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one - [T26256] | | CAS: | 893441-85-5 | | MF: | C14H18BNO3 | | MW: | 259.11 | | EINECS: | 200-589-5 | | Product Categories: | | | Mol File: | 893441-85-5.mol |  |
| | 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one Chemical Properties |
| density | 1.16±0.1 g/cm3 (20 ºC 760 Torr) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | Appearance | White to yellow Solid |
| | 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one Usage And Synthesis |
| Uses | 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one is useful for preparation of imidazopyridazines as therapeutic kinase inhibitors. | | Synthesis | The general procedure for the synthesis of 2-oxoindoline-6-boronic acid pinacol ester from 6-bromo-2-indolone and bis(pinacolato)diboron (898 mg, 3.54 mmol), potassium acetate (694 mg, 7.07 mmol) and Pd(dppf)Cl2-CH2Cl2 (96.0 mg, 0.118 mmol). The above mixture was dissolved in 1,2-dimethoxyethane (DME, 17 mL). The reaction system was heated and reacted at 80 °C overnight. Upon completion of the reaction, the contents of the four reaction vials were combined, the reaction solution was concentrated and purified by column chromatography (cyclohexane/ethyl acetate as eluent) to afford the target compound, 2-oxoindoline-6-boronic acid pinacol ester, as a white solid (2.27 g, 75% yield, 80% purity). The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3): δ 8.57 (broad single peak, 1H), 7.48 (double peak, J=7.3 Hz, 1H), 7.31 (single peak, 1H), 7.23 (double peak, J=7.3 Hz, 1H), 3.55 (single peak, 2H), 1.33 (single peak, 12H).LC-MS (ESI, m/z) analysis showed that: retention time was 0.5 mm. z) analysis showed retention time Rt = 2.75 min and molecular ion peak m/z = 260 ([M+H]+, HPLC method E). | | References | [1] Patent: WO2015/144290, 2015, A1. Location in patent: Page/Page column 85
[2] Patent: WO2015/39172, 2015, A1. Location in patent: Page/Page column 60
[3] Patent: WO2011/15641, 2011, A1. Location in patent: Page/Page column 128
[4] Patent: WO2011/101640, 2011, A1. Location in patent: Page/Page column 106
[5] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 120 |
| | 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one Preparation Products And Raw materials |
|