Electric Literature of 320734-35-8, A common heterocyclic compound, 320734-35-8, name is 7-Bromooxindole, molecular formula is C8H6BrNO, 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.
To a cooled (-78C) solution of 7-bromooxindole (4.7g; 22.16 mmol) and N,N,N?, N?tetramethylethylenediamine (10.97 mL; 73.17 mmol) in dry THF (230 mL) was slowly added n-butyllithium solution (19.S mL; 48.76 mmol; 2.S M in hexane). The solution was stirred for 30 minutes at the same temperature and then, iodomethane (1.65 mL; 26.6 mmol) was added slowly. The reaction mixture was stirred at -20C for 1.5h, then,quenched with a saturated aqueous solution of NH4C1 and extracted with EtOAc.The organic layer was sried over MgSO4, filtered and concentrated in vacuo. The resultingcrude material was purified by silica gel chromatography (mobile phase: heptane/EtOAc)to afford, after solvent evaporation, 1.3 g (22%) of intermediate 217.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (419 pag.)WO2018/2219; (2018); A1;,
Indoline – Wikipedia,
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