Reference of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.
6-Bromoisoindolin-l-one (CAS 675109-26-9) (1.61 g, 7.58 mmol, 1.05 equiv.) was suspended in 32 ml of THF and cooled to 0-5C. Sodium hydride (60% dispersion in mineral oil) (318 mg, 7.94 mmol, 1.1 equiv.) was added at 0-5C. The reaction mixture was stirred at room temperature for 15 minutes and then cooled to 0-5C. Methyl (2RS)-2-bromo-2-(5-fluoro-2- methoxyphenyl)acetate (CAS 1368458-30-3) (2.00 g, 7.22 mmol) dissolved in 8.0 ml of THF was added dropwise at 0-5C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated NH4CI- solution and extracted with ethyl acetate. The aqueous layer was backextracted with ethyl acetate. The organic layers were washed with water and brine. The organic layers were combined, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with an ethyl acetate:heptane 0: 100 to 50:0 gradient to obtain the desired methyl (2RS)-2-(6-bromo-l-oxo- isoindolin-2-yl)-2-(5-fluoro-2-methoxy-phenyl)acetate (2.202 g, 75 % yield) as a yellow foam, MS: m/e = 408.0/410.0 (M+H+).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; C4 THERAPEUTICS, INC.; JAESCHKE, Georg; RICCI, Antonio; RUEHER, Daniel; STEINER, Sandra; DUPLESSIS, Martin; NAGEL, Yvonne Alice; KUHN, Bernd; (60 pag.)WO2018/220149; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem