Methyl iodide → [7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester

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To a solution of [7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-carbamic acid tert-butyl ester (0.36 g, 0.9 mmol) in dry DMF (9 mL) was added cesium carbonate (1.04 g, 3.19 mmol) followed by neat methyl iodide (0.064 mL, 1.03 mmol). The mixture was stirred at room temperature for 3.5 hr, extracted into ethyl acetate (150 mL), washed with water (2×50 mL) and brine (50 mL), dried over sodium sulfate, filtered, concentrated in vacuo and dried to give 0.34 g (93%) of pure [7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester. RP-HPLC: 5.89 min; ES-MS (M+H)+=414.0; 1H-NMR (DMSO-d6) δ (ppm): 1.33 (s, 9), 3.20 (s, 3), 6.75 (d, 1), 7.52 (d, 1), 7.80 (d, 2), 7.83 (d, 1), 7.93 (d, 1), 8.35 (d, 2).

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