Reaction Steps
Prepared according to procedure Y by stirring 4-chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline (50 mg, 0.14 mmol), 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (44.9 mg, 0.16 mmol), XPhos precatalyst (20.1 mg, 0.027 mmol), sodium tert-butoxide (32.7 mg, 0.34 mmol), and toluene (1.5 mL) at 95° C. for 18 h. Purification by reverse-phase HPLC (0-70% acetonitrile in water) gave 1′-(5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-4-quinolinyl)-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 7.62-7.76 (1H, m), 7.24-7.33 (1H, m), 7.13-7.23 (1H, m), 6.98-7.09 (2H, m), 6.87-6.98 (1H, m), 6.48-6.60 (1H, m), 5.42-5.51 (1H, m), 3.67-3.76 (1H, m), 3.50-3.67 (2H, m), 3.20-3.28 (4H, m), 2.94-3.14 (2H, m), 2.59-2.65 (1H, m), 2.48-2.59 (6H, m), 1.71-1.88 (2H, m), 1.50-1.55 (1H, m), 1.38-1.46 (2H, m), 1.23-1.38 (1H, m), 1.07-1.19 (1H, m), 0.70-0.75 (1H, m). Mass Spectrum (ESI) m/e=607.0 (M+1).
