20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-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.
Under argon, 2.64 g (66 mmol) of sodium hydride (60% in mineral oil) were suspended in 25 ml of THF and cooled to 0 C. A solution of 4.00 g (18.86 mmol) of 5-bromo-1,3-dihydro-2H-indol-2-one in 25 ml of DMF was added dropwise and the mixture was stirred at 0 C. for 30 min. Subsequently, 4.11 ml (66 mmol) of methyl iodide were slowly added dropwise thereto, then the reaction mixture was warmed to RT and stirring continued at this temperature overnight. For workup, the mixture was poured onto 200 ml of 1M hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were washed with water, then a saturated sodium chloride solution, dried over sodium sulphate and concentrated on a rotary evaporator. The residue was dissolved in 200 ml of acetonitrile and the mineral oil was extracted with n-pentane. The acetonitrile phase removed was concentrated on a rotary evaporator and the remaining brownish solid was dried under HV. This gave 4.45 g (84% of theory) of the title compound in 91% purity. LC-MS (Method 3): Rt=1.18 min; m/z=254, 256 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.27 (s, 6H), 3.12 (s, 3H), 6.99 (d, 1H), 7.45 (dd, 1H), 7.60 (d, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoindolin-2-one, its application will become more common.
Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Fuerstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Tersteegen, Adrian; Zubov, Dmitry; Kast, Raimund; Schamberger, Jens; Schaefer, Martina; Boerngen, Kirsten; US2015/148340; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem