169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H4F3NO3
General procedure: The title compound was synthesized in one step from commercially available starting materials according to the following procedure. Into a 20mL microwave reaction vial, containing a magnetic stir bar, were weighed 5-(trifluoromethoxy)isatin (460mg, 2.0mmol), K2CO3 (550mg, 4.0mmol), KI (33mg, 0.20mmol), followed by acetonitrile (20mL, 0.1M) and 2-bromoethyl phenyl ether (480mg, 2.4mmol). After being sealed with a crimp cap, the vessel was placed in a microwave reactor and heated to 160C for 10min, with magnetic stirring. After cooling to ambient temperature, the reaction was diluted with CH2Cl2 (?20mL) and washed with brine. The organic layer was separated and dried over Na2SO4. Solvent was removed under reduced pressure and the crude product was purified via flash column chromatography (silica gel, hexane/ethyl acetate, 0-50% ethyl acetate gradient). Product containing fractions were combined and the solvents removed under reduced pressure to obtain 583mg of ML326 (83% yield) as a red-orange powder. TLC Rf=0.79 (hexane/ethyl acetate 1:1); 1H NMR (400MHz, CDCl3 calibrated to 7.26) delta 7.52-7.46 (m, 2H), 7.31-7.25 (m, 3H), 6.98 (t, J=7.4Hz, 1H), 6.82 (d, 2H), 4.28 (t, J=5.0Hz, 2H), 4.17 (t, J=5.0Hz, 2H); 13C NMR (125MHz, CDCl3 calibrated to 77.16) delta 182.25, 158.27, 157.93, 150.01, 145.44, 131.02, 129.78, 121.75, 118.32, 114.39, 112.89, 65.94, 40.62; HRMS calcd for C17H13NO4F3[M+H+]; 352.0797 found: 352.0795.
The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Gentry, Patrick R.; Bridges, Thomas M.; Lamsal, Atin; Vinson, Paige N.; Smith, Emery; Chase, Peter; Hodder, Peter S.; Engers, Julie L.; Niswender, Colleen M.; Scott Daniels; Jeffrey Conn; Wood, Michael R.; Lindsley, Craig W.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2996 – 3000;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem