Sodium Carbonate → N-(2-(1-cyclohexen-1-yl)-5-(4-morpholinyl)-3-pyridinyl)-5,7-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine

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A dry flask containing 5-bromo-2-cyclohexenylpyridin-3-amine (0.19 g, 0.76 mmol) in dry DMF (5.0 mL) was cooled to 0° C., then sodium hydride, 60% dispersion in mineral oil (0.061 g, 1.53 mmol) was added carefully in portions. The mixture was stirred at 0° C. for 15 min, then 4-chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.26 g, 0.91 mmol) was added in portions. Upon complete addition, the mixture was warmed to 70° C. After 18 h, the incomplete reaction was cooled to rt then was carefully treated with 10% sodium carbonate solution. The black mixture was subsequently extracted five times with DCM:MeOH (90:10). The organic extraction was then washed one time with brine and dried over anhydrous magnesium sulfate. After filtration and concentration, the black residue was treated with MeOH and placed on the rotovap. (without vac.) in a 45° C. water bath. After 30 min, the solid was filtered and rinsed twice with MeOH to afford a tan solid as N-(2-(1-cyclohexen-1-yl)-5-(4-morpholinyl)-3-pyridinyl)-5,7-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.72 (1H, d, J=3.9 Hz), 8.15 (3H, m), 7.89 (1H, d, J=7.8 Hz), 7.68 (1H, d, J=9.0 Hz), 7.53 (1H, ddd, J=7.6, 4.9, 1.2 Hz), 7.46 (1H, m.), 7.01 (1H, s), 5.92 (1H, m.), 2.37 (1H, dd, J=3.5, 1.8 Hz), 2.16 (3H, s), 1.99 (2H, m), 1.63 (2H, m), 1.46 (2H, m.).

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