Synthetic Route of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A mixture of the appropriate amine (1 mmol) and the appropriate benzyl bromide (1 mmol) in DMF (0.5 M) was stirred at room temperature up to 100 C until completion of the reaction (up to5 days). The reaction mixture was either diluted with EtOAc and the resultant precipitate filtered to give pure product or quenched with sat. NaHCO3 and extracted with EtOAc. Crude material was purified either by automated flash chromatography (EtOAc:hexanes mixture) or by preparative HPLC to give the desired compound in 10-50% yield; ?H NIVIR (400 MHz, DMSO-d6)10.80 (s, 1H), 7.55 (dd, J= 13.2, 8.2 Hz, 3H), 7.48 – 7.40 (m, 1H), 7.15 (t, J 4.7 Hz, 1H), 7.03 (d, J 2.1 Hz, 1H), 6.97 (dd, J 8.4, 2.1 Hz, 1H), 4.53 (d, J= 4.6 Hz, 2H). ?3C NIVIR (101 1VIHz, DMSO) 170.07, 169.81, 154.14, 136.18, 135.86, 133.44, 131.11, 129.23, 125.00, 118.91, 115.96, 105.49, 43.32.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.
Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem