Morpholine → 5,7-difluoro-N-(2-(3-methoxyphenyl)-5-(4-morpholinyl)-3-pyridinyl)-3-methyl-2-(2-pyridinyl)-4-quinolinamine

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of N-(5-bromo-2-(3-methoxyphenyl)pyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine (0.103 g, 0.19 mmol), morpholine (0.04 mL, 0.46 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.019 g, 0.021 mmol), 2-dicyclohexylphosphino-2,4,6,-triisopropylbiphenyl (0.0188 g, 0.039 mmol), and sodium tert-butoxide (0.058 g, 0.608 mmol) in dry toluene (3.0 mL) was purged three times with argon and placed under vacuum three times, then the mixture was heated to 100° C. After 21.5 h, the reaction was cooled to rt, then treated with water. 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 basic alumina (0-30% EtOAc in hexanes) to afford a light yellow solid as 5,7-difluoro-N-(2-(3-methoxyphenyl)-5-(4-morpholinyl)-3-pyridinyl)-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (500 MHz, CDCl3) δ ppm 8.73 (1H, m), 8.02 (1H, d, J=2.4 Hz), 7.95 (2H, m), 7.63 (1H, m.), 7.50 (4H, m), 7.05 (2H, m), 6.56 (1H, m.), 3.94 (7H, m), 3.32 (4H, m), 2.24 (3H, s). Mass Spectrum ESI (pos.) m/e: 540.3 (M+H)+.

Provenance & Evidence