Application of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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.
To a stirred solution of Boc-2,4-dichloro-d-phenylalanine (0.280 g, 0.84 mmol), EDC¡¤HCl (0.161 g, 0.84 mmol), HOBt (0.170 g, 1.26 mmol) and DIPEA (1.12 mL, 6.29 mmol) in DMF (2.0 mL), isoindoline (0. 10 g, 0.84 mmol) was added. The reaction was stirred at room temperature for 24 h. Upon completion, solvent was removed under reduced pressure and the crude was purified using column chromatography to provide desired coupled product in 78% yield. To the purified compound (0.21 g, 0.48 mmol) was added 1 M HCl (9.5 mL, 1 M in Et2O). After 4 h of stirring, the solvent was removed under reduced pressure to afford target compound 4 as a white solid. 1H NMR (400 MHz, CD3OD): delta 3.42 (d, 2H, 8.0 Hz), 4.24 (d, 1H, 12 Hz), 4.63 (t, 1H, 8.0 Hz), 4.72 (d, 1H, 16 Hz), 4.89 (d, 1H, 16 Hz), 5.00 (d, 1H, 12 Hz), 7.26 (m, 1H), 7.35 (m, 4H), 7.44 (d, 1H, 8.0 Hz), 7.54 (d, 1H, 4.0 Hz) 13C NMR (100.6 MHz, CD3OD): delta 35.3, 52.1, 53.2, 53.6, 123.7, 123.9, 128.9, 129.1, 129.2, 130.7, 132.1, 132.4, 136.0, 136.3, 136.4, 136.6, 168.1 HRMS (TOF-MS) Exact mass calcd for C17H16Cl2N2O [M+H]+: 335.0718, found: 335.0712.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindoline, its application will become more common.
Reference:
Article; Whitehead, Lewis; Dobler, Markus R.; Radetich, Branko; Zhu, Yanyi; Atadja, Peter W.; Claiborne, Tavina; Grob, Jonathan E.; McRiner, Andrew; Pancost, Margaret R.; Patnaik, Anup; Shao, Wenlin; Shultz, Michael; Tichkule, Ritesh; Tommasi, Ruben A.; Vash, Brian; Wang, Ping; Stams, Travis; Bioorganic and Medicinal Chemistry; vol. 19; 15; (2011); p. 4626 – 4634;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem