Electric Literature of 552330-86-6, A common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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.
Example 271: (S)- l-Oxo-N-((4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)- pyridin-2-yl)methyl)isoindoline-5-carboxamide.Step 1. Methyl l-oxoisoindoline-5-carboxylate.To a 25 mL round bottom flask containing 5-bromo-2,3-dihydro-isoindol- 1-one (500 mg, 2.36 mmol), was added TEA. The resulting mixture was then stirred at 23 C for 2 min. At this time, MeOH (954 mu,, 23.58 mmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (54.6 mg, 0.094 mmol)(Xantphos) and palladium(II) acetate (10.59 mg, 0.047 mmol) were added to the flask. The reaction mixture was then flushed with argon and then with carbon monoxide. The flask was fitted with a rubber septa and a balloon of carbon monoxide was inserted through septa. The flask was stirred at 70 C overnight under carbon monoxide, allowed to cool, diluted with EtOAc (50 mL) and filtered through Celite eluting with EtOAc (300 mL). The solid remaining on the Celite pad was washed with DCM (200 mL) and DCM/MeOH (10: 1)(150 mL) and the filtrates concentrated to give a pale green solid (800 mg). A portion of this material was taken on to the next reaction with no further purification.
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; AMGEN INC.; BISWAS, Kaustav; BROWN, James; CHEN, Jian, J.; GORE, Vijay, Keshav; HARRIED, Scott; HORNE, Daniel, B.; KALLER, Matthew, R.; LIU, Qingyian; MA, Vu, Van; MONENSCHEIN, Holger; NGUYEN, Thomas, T.; YUAN, Chester, Chenguang; ZHONG, Wenge; ST. JEAN, David, J., Jr.; WO2012/177893; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem