Reaction Steps
Prepared according to procedure Y using 4-chloro-3-methyl-2-phenyl-1,8-naphthyridine (46.3 mg, 0.182 mmol), 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (50 mg, 0.182 mmol), sodium tert-butoxide (34.9 mg, 0.363 mmol) and XPhos precatalyst (0.0182, 13.5 mg). Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 1′-(3-methyl-2-phenyl-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 9.12 (1H, dd, J=4.1, 2.0 Hz), 8.12 (1H, dd, J=8.4, 2.0 Hz), 7.71-7.77 (2H, m), 7.65 (1H, d, J=2.3 Hz), 7.47-7.56 (3H, m), 7.43 (1H, dd, J=8.3, 4.2 Hz), 5.80 (1H, d, J=2.3 Hz), 4.12-4.21 (2H, m), 4.02 (2H, q, J=9.6 Hz), 3.71-3.80 (4H, m), 3.56-3.65 (2H, m, J=11.4, 11.4, 2.5, 2.4 Hz), 2.95-3.05 (4H, m), 2.28-2.41 (5H, m), 1.75-1.90 (2H, m). Mass Spectrum (ESI) m/e=494.2 (M+1).
