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With potassium carbonate; In N,N-dimethyl-d6-formamide; at 80℃; for 10.0h;
To a solution of compound 24 (0.31 g, 2 mmol) and K2CO3 (1.38 g, 10 mmol) in anhydrous N,N-dimethylformamide (DMF) (5 ml) was added CH3I (0.35 g, 2.5 mmol), and the reaction mixture was stirred for 10 h at 80 C. After cooling down the reaction to room temperature was added DCM (50 ml) to the solution, and washed with saturated NaHCO3. The organic layer dried over by MgSO4 and concentrated in vacuo to give the product 25 (0.34 g, 92%). 1H NMR (DMSO-d6, 400 MHz): delta 7.41-7.36 (m, 1H), 7.23-7.21 (m, 1H), 7.12-7.09 (m, 1H), 2.95 (s, 6H). ESI-HRMS: m/z calcd for C8H9FN2O2 [M+H]+ 185.0682 found 185.0749.
With potassium carbonate; In N,N-dimethyl-formamide; at 5 - 20℃; for 63.0h;
The (4-fluoro-3-nitrophenyl)dimethylamine can be prepared in the following way: 13.27 g (96 mmol) of potassium carbonate are added, at a temperature in the region of 20 C., under an argon atmosphere, to 5 g (32 mmol) of 4-fluoro-3-nitroaniline in solution in 50 cm3 of dimethylformamide, followed, at a temperature in the region of 5 C., by 4.6 cm3 (73.6 mmol) of iodomethane. After stirring for 63 hours at a temperature in the region of 20 C., the reaction mixture is poured into 100 cm3 of water and then extracted with 3 times 100 cm3 of dichloromethane. The organic phases are combined, washed with 3 times 100 cm3 of water, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (2.7 kPa), to give 5.5 g of a residue which is purified by flash chromatography [eluent: ethyl acetate/cyclohexane (2/8 by volume)]. After concentration under reduced pressure of the fractions containing the expected product, 2.78 g of (4-fluoro-3-nitrophenyl)dimethylamine are obtained in the form of an orange-red solid; MS-ES+: m/z=185(+)=(M+H) (+)
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