Analyzing the synthesis route of 496-12-8

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 496-12-8.

496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, its 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 solution of 6-bromo-4-chlorobenzo[c][1,2,5]oxadiazole (372 mg, 1.6 mmol) in NMP (3 mL) in a 4 dram vial was added isoindoline (238 mg, 2 mmol) and triethylamine (400 muL, 2.9 mmol). A cap was tightly fitted and the reaction was heated at 85 C. O/N. The reaction was worked up by diluting with EtOAc (60 mL) and washing with 1M HCl (3*20 mL) and brine (1*20 mL). The organic phase was dried with MgSO4 filtered and concentrated in vacuo. The crude material was purified by flash column chromatography (9:1 Hex/EtOAc) to give 208 mg (41% yield) of 6-bromo-4-(isoindolin-2-yl)benzo[c][1,2,5]oxadiazole. 1H NMR (300 MHz, CDCl3) delta=7.38 (m, 4H), 7.26 (s, 1H), 6.14 (s, 1H), 5.14 (s, 4H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 496-12-8.

Reference:
Patent; Treventis Corporation; Reed, Mark A.; Wood, Thomas K.; Banfield, Scott C.; Barden, Christopher J.; Yadav, Arun; Lu, Erhu; Wu, Fan; (204 pag.)US2017/174641; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem