Electric Literature of 264916-06-5,Some common heterocyclic compound, 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, molecular formula is C13H18N2O2, 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.
Step-1: Synthesis of tert-butyl 5-((1-(2-(tert-butyl)pyridin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate To a stirred solution of 1-(2-(tert-butyl)pyridin-4-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-indazol-3-one (120 mg, 0.34 mmol, 1.0 eq) in (2.0 mL) of toluene was added m-CPBA (91 mg, 0.37, 1.1 eq) and allowed to stir at rt for 30 minutes. tert-butyl 5-aminoisoindoline-2-carboxylate (102 mg, 408 mmol, 1.2 eq) and DIPEA (0.30 mL, 1.7 mmol, 5.0 eq) were added and allowed to stir at rt for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography to afford the desired product, tert-butyl 5-((1-(2-(tert-butyl)pyridin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate (40 mg, 21.73%) as brown solid.
The synthetic route of 264916-06-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem