Reaction Steps
Prepared according to procedure Y by using 4-chloro-3-methyl-2-(pyridin-2-yl)-1,7-naphthyridine (70 mg, 0.274 mmol), 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (75 mg, 0.274 mmol), sodium tert-butoxide (52.6 mg, 0.548 mmol) and XPhos precatalyst (20 mg, 0.027 mmol) with heating in toluene (4 mL) for 2 h at 110° C. Purification by reverse phase HPLC (to 10 50% acetonitrile water) gave 1′-(3-methyl-2-(2-pyridinyl)-1,7-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 9.60 (1H, d, J=1.0 Hz), 8.75 (1H, dt, J=4.8, 1.5 Hz), 8.55 (1H, d, J=5.9 Hz), 7.92-8.01 (2H, m), 7.65 (1H, d, J=2.3 Hz), 7.51 (1H, dd, J=5.7, 1.0 Hz), 7.43 (1H, ddd, J=6.0, 4.8, 2.9 Hz), 5.84 (1H, d, J=2.3 Hz), 4.12-4.20 (2H, m), 3.93-4.05 (2H, m), 3.71-3.77 (4H, m), 3.52-3.62 (2H, m), 2.95-3.12 (4H, m), 2.47 (3H, s), 2.28-2.43 (2H, m), 1.69-1.88 (2H, m). Mass Spectrum (ESI) m/e=495.0 (M+1).
