Simple exploration of 1504-06-9

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyloxindole, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 1504-06-9, name is 3-Methyloxindole, 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 1504-06-9, category: indolines-derivatives

Step 1 : Preparation of 3-methyl-5-(3-trifluoromethylphenyl)- 1 ,3-dihydroindol-2-oneA solution of 3-methyloxindole (5.06 g, 34.4 mmol) in iV,iV-dimethylformamide (60 mL) was cooled to 0 0C. N-Bromosuccinimide (6.23 g, 35.0 mmol) was added, and the resulting solution was stirred for 18 hours while slowly warming to room temperature. The reaction was then diluted with ethyl acetate (100 mL) and washed with 1 :1 saturated aqueous NaCl solutuion:H2O (3 x 75 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated under reduced pressure to give a solid that was used without further purification in the next step described below.A mixture of the crude product described above (1.02 g5 4.51 mmol), 3- (trifluoromethyl)phenylboronic acid (0.983 g, 5.18 mmol), sodium carbonate (0.884 g, 8.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.252 g, 0.218 mmol) in ethylene glyclol dimethyl ether (8.0 mL) and H2O (1.0 mL) was warmed to 80 0C. After 20 hours, the mixture was cooled to room temperature, poured into 1 : 1 saturated aqueous NaCl solution:H2O (50 mL), and extracted with ethyl acetate (3 x 50 mL). The organic extracts were combined, dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel Biotage 4OM, eluting with 10-35% ethyl acetate/hexanes, to give 3-methyl-5-(3-trifluoromethylphenyl)-l,3-dihydroindol-2-one as a white solid.1H NMR (CDCl3): delta 8.27 (br s, 1 H), 7.79 (s, 1 H), 7.72 (d, I H1 J = 7.3 Hz), 7.56 (m, 2 H), 7.46 (m, 2 H), 6.99 (m, 1 H), 3.55 (dd, 1 H, J = 15.3, 7.8 Hz), 1.57 (d, 3 H, J = 7.7 Hz) MS: m/e 292.41 (M + H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyloxindole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem