GENERAL METHODS: 6-Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved in N,N-dimethylformamide (DMF, 150 mL) under heating conditions and subsequently cooled to 0°C. The reaction was carried out under nitrogen protection by slowly adding sodium hydride (NaH, 415 mg, 10.4 mmol) to the reaction system. Sodium hydride (NaH, 415 mg, 10.4 mmol) was slowly added to the reaction system under nitrogen protection and the reaction mixture was stirred at 0 °C for 30 min. Subsequently, iodomethane (0.65 mL, 10.4 mmol) was added dropwise and the reaction system was gradually warmed up to room temperature with continued stirring for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of a small amount of water, followed by evaporation of DMF under reduced pressure to give a yellow oily residue. The residue was dissolved in ethyl acetate (EtOAc, 150 mL), washed sequentially with water (3 x 100 mL), saturated saline (100 mL) and dried with anhydrous sodium sulfate (Na2SO4). The organic solvent was removed by concentration under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography (eluent: 10% acetone/dichloromethane). N-methyl-6-bromoisoindolin-1-one was finally obtained as a very light yellow crystalline solid (1.64 g, 80% yield).1H NMR (400 MHz, (CD3)2SO) δ: 7.85 (dd, J = 1.5, 0.6 Hz, 1H), 7.66 (dd, J = 8.0, 1.7 Hz, 1H), 7.59 (d, J = 8.0 Hz , 1H), 4.46 (s, 2H), 3.05 (s, 3H).LRMS (APCI) Calculated C9H8BrNO2 [M+H]+: 226, 228, Measured: 226, 228.
