| Identification | Back Directory | [Name]
tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxyl | [CAS]
905273-91-8 | [Synonyms]
isoindoline-2-carboxylate
2-BOC-1H-Isoindoline-5-boronic acid pinacol ester
2-Boc-1,3-dihydro-isoindole-5-boronic acid picol ester
2-Boc-1,3-dihydro-isoindole-5-boronic acid pinacol ester
2-Boc-5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-isoindole
tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxyl
tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydroisoindole-2-carboxylate
tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-isoindole-2-carboxylate
5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester
2H-Isoindole-2-carboxylicacid, 1,3-dihydro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-,1,1-dimethylethyl ester | [Molecular Formula]
C19H28BNO4 | [MDL Number]
MFCD11226842 | [MOL File]
905273-91-8.mol | [Molecular Weight]
345.24 |
| Chemical Properties | Back Directory | [Boiling point ]
442.5±45.0 °C(Predicted) | [density ]
1.11±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
-1?+-.0.20(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Uses]
tert-??Butyl 5-??(4,??4,??5,??5-??tetramethyl-??1,??3,??2-??dioxaborolan-??2-??yl)??isoindoline-??2-??carboxylate is a reactant in the synthesis of tyrosine kinase inhibitors in the treatment of proliferative diseases. | [Synthesis]
General procedure: 5-bromo-2-(tert-butoxycarbonyl)isoindoline (1.2 g, 4 mmol), bis(pinacolato)diboron (2 g, 8 mmol) and DMSO (20 mL) were added to the reaction flask followed by AcOK (1.6 g, 16 mmol). Pd(dppf)Cl2-CH2Cl2 (327 mg, 0.4 mmol) was added under nitrogen protection. The reaction mixture was heated and stirred at 90°C for 12 hours. After completion of the reaction, it was cooled to room temperature and the reaction solution was poured into EtOAc/H2O (300 mL/100 mL). The organic phase was separated, washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 20/1) to afford N-Boc-isoindoline-5-boronic acid pinacol ester as a yellow oil (1 g, 73%).MS (ESI, cationic) m/z: 290.2 [M-56 + 1]; 1H NMR (400 MHz, CDCl3) δ (ppm): 7.68- 7.74 (m, 2H), 7.23-7.30 (m, 1H), 4.64-4.70 (m, 4H), 1.53 (s, 9H), 1.36 (s, 12H). | [References]
[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 2, p. 199 - 210
[2] Patent: WO2014/89324, 2014, A1. Location in patent: Paragraph 0237
[3] Patent: CN104016979, 2017, B. Location in patent: Paragraph 0606; 0607; 0608; 0609
[4] Patent: US2008/171754, 2008, A1. Location in patent: Page/Page column 103
[5] Patent: WO2010/10186, 2010, A1. Location in patent: Page/Page column 58 |
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