Reaction Steps
Prepared according to procedure Y using 4-chloro-2-(3,5-difluorophenyl)-3-methyl-1,8-naphthyridine (60 mg, 0.206 mmol), 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (56.8 mg, 0.206 mmol), sodium tert-butoxide (39.7 mg, 0.413 mmol) and XPhos precatalyst (15 mg, 0.021 mmol). Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 1′-(2-(3,5-difluorophenyl)-3-methyl-1,8-naphthyridin-4-yl)-6′-(4-morpholinyl)-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine]. 1H NMR (400 MHz, chloroform-d) δ ppm 9.14 (1H, dd, J=4.1, 2.0 Hz), 8.13 (1H, dd, J=8.4, 2.0 Hz), 7.67 (1H, d, J=2.3 Hz), 7.46 (1H, dd, J=8.3, 4.2 Hz), 7.21-7.33 (2H, m), 6.88-7.00 (1H, m), 5.78 (1H, d, J=2.3 Hz), 4.14-4.21 (2H, m), 3.93-4.07 (2H, m), 3.70-3.80 (4H, m), 3.52-3.66 (2H, m, J=11.3, 11.3, 2.5, 2.2 Hz), 2.91-3.07 (4H, m), 2.27-2.43 (5H, m), 1.70-1.89 (2H, m). Mass Spectrum (ESI) m/e=530.2 (M+1).
