Potassium Carbonate → N-(3-((2-(3,5-difluorophenyl)-3-methyl-1,8-naphthyridin-4-yl)amino)-5-(4-morpholinyl)phenyl)acetamide

Participants

Reaction Steps

Prepared according to Procedure X by stirring N-(3-amino-5-morpholinophenyl)-acetamide (48.6 mg, 0.206 mmol), 4-chloro-2-(3,5-difluorophenyl)-3-methyl-1,8-naphthyridine (50 mg, 0.172 mmol), palladium (II) acetate (3.9 mg, 0.017 mmol), XPhos (16.4 mg, 0.034 mmol), potassium carbonate (60 mg, 0.43 mmol), and 1 mL tert-butanol at 85° C. for 24 h. Purification by reverse-phase HPLC afforded N-(3-((2-(3,5-difluorophenyl)-3-methyl-1,8-naphthyridin-4-yl)amino)-5-(4-morpholinyl)phenyl)acetamide. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.84 (1H, dd, J=4.1, 2.0 Hz), 8.21-8.28 (2H, m), 7.23-7.27 (1H, m), 7.10-7.14 (1H, m), 7.04-7.10 (2H, m), 6.85-6.91 (1H, m), 6.45-6.50 (1H, m), 6.14-6.21 (2H, m), 3.77-3.86 (4H, m), 3.09-3.15 (4H, m), 2.33 (3H, s), 1.99 (3H, s). Mass Spectrum (ESI) m/e=490.0 (M+1).

Provenance & Evidence