Career opportunities within science and technology are seeing unprecedented growth across the world, and those who study chemistry or another natural science at university now have increasingly better career prospects. Synthetic Route of 20870-90-0
5-bromo-1-methylindolin-2-one (500 mg, 2.21 mmcl) was dissolved in dry THF (5 mL). The solution was purged with N2 and Pd2(dba)3 (127 mg, 0.14 mmol) and XPhos (132 mg, 0.28 mmol) were added to the solution. The freshly prepared bromo[1-(methoxycarbonyl)cyclopropyl]zinc (6.94 mL, 5.55 mmol) was added slowly as a solution in THF (approx. 0.8 M). The resulting mixture was heated at 70C for 1 h30. Partial conversion was obersved by LCMS. The mixture was heated at 70C overnight, no change in profile. Further Pd2(dba)3 (127 mg, 0.14 mmol) and XPhos (132 mg, 0.28 mmol) were added followed by bromo[1-(methoxycarbonyl)cyclopropyl]zinc (6.94 mL, 5.55 mmol). Heating to 70C was continued until almost complete conversion was observed (1h30).The mixture was cooled to rt and was quenched with water and EtOAc. The mixture was filtered through a pad of Celite. After phases separation, the remaining organic layer was dried over Mg504, filtered and the solution was concentrated to dryness. The crude material was purified by column chromatography eluting with a gradient of Cyclohexane/EtOAc from [100:0] to [65:35]. The product fractions were combined and concentrated to dryness to afford methyl 1-(1- methyl-2-oxo-2,3-dihydro-1 H-indol-5-yl)cyclopropane-1 -carboxylate Ex.75a (99 mg, 18%) as pale orange solid. 1H NMR (300 MHz, DMSO-d6, din ppm): 1.12- 1.16 (m, 2H), 1.44-1.48 (m, 2H), 3.09 (s, 3H), 3.51 (s, 2H), 3.52 (s, 3H), 6.88 (d, 1H, J=8.7Hz), 7.21 (d, 1H, J=1.8Hz), 7.23 (d, 1H, J=1.8Hz).
We very much hope you enjoy reading the articles and that you will join us to present your own research about 5-Bromo-1-methyl-2-oxoindoline.
Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem