Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, belongs to indolines-derivatives compound, 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 2058-72-2, category: indolines-derivatives
A stirred brown solution of 5-bromo-1-methylindoline-2,3-dione (500 mg, 2.083 mmol) in DCM (10 ml.) was cooled down to 0C and bis(2-methoxyethyl)aminosulfur trifluoride (1.152 ml, 3.12 mmol) was slowly added into it, followed by EtOH (0.036 ml_, 0.625 mmol). The reaction mixture was allowed to warm up and stir overnight at RT. Bis(2-methoxyethyl)aminosulfur trifluoride (1.152 ml_, 3.12 mmol) was added and the mixture was stirred 8 hr at RT. The reaction was quenched with saturated aqueous Na2C03 solution and both phases were separated. The organic layer was washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (Cyclohexane / 0 to 50% EtOAc). The resulting solid was diluted with MeOH (2 ml_), sonicated, cooled down to 0C and filtrated off to afford the title product (183 mg, 0.698 mmol) as a beige solid. Rt = 1.07 min (UPLC- MS); 1H NMR (400 MHz, DMSO-d6) d ppm 3.17 (s, 3 H) 7.22 (d, J=8.44 Hz, 1 H) 7.84 (d, J=8.44 Hz, 1 H) 8.01 (s, 1 H).
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Reference:
Patent; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem