496-12-8, Adding some certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 496-12-8.
To a solution of 6-bromo-4-chlorobenzo[c][l ,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 x 20 mL) and brine (1 x 20 mL). The organic phase was dried with MgS04 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][l ,2,5]oxadiazole. lU NMR (300 MHz, CDC13) delta = 7.38 (m, 4H), 7.26 (s, 1H), 6.14 (s, 1H), 5.14 (s, 4H). To a solution of the afore mentioned material, (200 mg, 0.6 mmol) in DME (4 mL) / Na2C03 (0.9 mL) was added 3- formyl-phenylboronic acid (134 mg, 0.9 mmol) and Pd(P(Ph)3)4 (35 mg). The flask was then fitted with a reflux condenser, purged with argon and heated to 115 C O/N. The reaction was worked up by diluting with 1 M NaOH (40 mL) and extracting with EtOAc (3 x 20 mL). The organic phase was washed with brine, dried with MgS04 and concentrated in vacuo. The crude material was fused to Si02 (2 g) and purified by flash column chromatography (2:1 DCM / Hex) to give 190 mg (92 % yield). 1H NMR (500 MHz, CDC13) delta = 10.18 (s, 1H), 8.24 (m, 1H), 7.99 (dm, J = 8 Hz, 2H), 7.70 (t, J = 7 Hz, 1H), 7.44 (m, 4H), 7.26 (s, 1H), 6.30 (s, 1H), 5.25 (s, 4 H). To a stirring solution of the afore mentioned material, (190 mg, 0.55 mmol) and Rupert’s reagent (150 mg, 1.1 mmol) in DCM (5 mL) at 0 C was added TBAF (0.1 mL, 1 M THF, 0.1 mmol). After 30 min at low temperature the cold bath was removed and the reaction was allowed to come to RT. After 3 hours an excess of TBAF was added and the reaction was diluted with DCM. The organic phases were washed with saturated NFLCl, brine, and then dried with MgS04 and concentrated in vacuo. The crude material was passed through a plug of Si02 (DCM)and then purified by flash column chromatography (2: 1 DCM / Hex). 1H NMR (500 MHz, CDCI3) delta = 7.84 (s, 1H), 7.77 (dt, J = 7 Hz, 2 Hz, 1H), 7.60 (m, 2H), 7.43 (m, 4H), 7.23 (s, 1H), 6.25 (s, 1H), 5.31 (s, 4H), 5.2 (m, 1H), 2.68 (s, 1H).
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.; WO2014/31873; (2014); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem