Potassium Carbonate → N-(3-((5,7-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)phenyl)acetamide

Participants

Reaction Steps

Prepared according to Procedure X by stirring palladium (II) acetate (1.5 mg, 6.88 μmol), XPhos (9.9 mg, 0.021 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.040 g, 0.138 mmol), N-(3-amino-5-morpholinophenyl)acetamide (0.034 g, 0.144 mmol), potassium carbonate (0.048 g, 0.344 mmol), and tert-butanol at 110° C. for 2 h. Purification by reverse-phase HPLC (0-70% acetonitrile in water) afforded N-(3-((5,7-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)phenyl)acetamide as a yellow amorphous solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.69 (1H, dq, J=4.8, 1.0 Hz), 7.80-7.95 (3H, m), 7.59 (1H, ddt, J=9.6, 2.2, 1.0, 1.0 Hz), 7.37-7.44 (1H, m), 7.12-7.22 (2H, m), 7.01 (1H, ddd, J=13.8, 8.5, 2.5 Hz), 6.31-6.36 (1H, m), 6.23 (1H, t, J=2.2 Hz), 3.81-3.87 (4H, m), 3.15-3.22 (4H, m), 2.12 (3H, s), 2.10 (3H, s). Mass Spectrum (ESI) m/e=490.0 (M+1).

Provenance & Evidence