A stirred mixture of mostly N-(5-bromo-2-(4-methoxyphenyl)pyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine (0.093 g, 0.18 mmol), 2-dicyclohexylphosphino-2,4,6,-triisopropylbiphenyl (0.017 g, 0.035 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.017 g, 0.018 mmol), and sodium tert-butoxide (0.058 g, 0.60 mmol) in dry toluene (3.0 mL) was purged three times with argon and placed under vacuum three times, then morpholine (0.2 mL, 2.30 mmol) was added to the mixture by syringe. Upon complete addition, the mixture was heated to 100° C. After 23.5 h, the reaction was cooled to rt, then treated with 1M Na2CO3 solution. After extracting twice with DCM:MeOH (95:5), the organics were combined and dried over anhydrous magnesium sulfate. After filtration and concentration the residue was purified on silica gel (0-40% of 89:9:1 DCM:MeOH:ammonium hydroxide solution in DCM) to afford an impure light yellow film. This film was submitted to analytical group for SFC purification. After concentration, the residue was identified as 5,7-difluoro-N-(2-(4-methoxyphenyl)-5-(4-morpholinyl)-3-pyridinyl)-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.74 (1H, m), 8.05 (1H, m), 7.94 (2H, m), 7.76 (2H, m), 7.64 (1H, m), 7.42 (1H, m), 7.07 (3H, m), 6.99 (1H, m), 6.54 (1H, m), 3.92 (7H, m), 3.22 (4H, m), 2.22 (3H, s). Mass Spectrum ESI (pos.) m/e: 540.3 (M+H)+.
