Synthetic Route of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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.
Under nitrogen atmosphere, 70 mg of 5-bromo-1-oxo-isoindoline was dissolved in 2 ml of tetrahydrofuran, cooled down to 0C, and then 4 mg of N,N-dimethylaminopyridine and 144 mg of di-tert-butylcarbonate were added. The mixture was stirred at room temperature for 30 min. Methanol was added to the reaction solution, and the solvents were distilled outunder reduced pressure. Water was added to the residues, extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (ethyl acetate/hexane=1/2), to obtain 51.2 mg of the above compound as a white solid. 1HNMR(400MHz,CDCl3.)delta.:1.60(9H,s), 4.74(2H,s), 7.62-7.65(2H,m), 7.76(1H,d,J=8.0Hz). 1) Manufacture of 5-bromo-2-tert-butoxycarbonyl-1-oxo-isoindoline Under nitrogen atmosphere, 1.5 mg of 5-bromo-1-oxo-isoindoline was dissolved in 20 ml of tetrahydrofuran, cooled down to 0C. Then, 85 mg of N,N-dimethylaminopyridine and 3.0 ml of tert-butylcarbonate were added, and the mixture was stirred at room temperature for 30 min. Methanol was added to the reaction solution, and the solvents were distilled outunder reduced pressure. Water was added to the residues, extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (ethyl acetate/hexane=1/2), to obtain 300 mg of the above compound as a white solid. 1HNMR(400MHz,CDCl3.)delta.:1.60(9H,s), 4.74(2H,s), 7.62-7.65(2H,m), 7.76(1H,d,J=8.0Hz) ESI-MS Found:m/z 344.2[M+Na]+
Statistics shows that 5-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 552330-86-6.
Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1726585; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem