Reaction Steps
Prepared according to procedure Y by stirring 4-chloro-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinoline (45 mg, 0.148 mmol), 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (48.8 mg, 0.177 mmol), XPhos precatalyst (10.9 mg, 0.015 mmol), sodium tert-butoxide (28.4 mg, 0.295 mmol), and toluene (1.6 mL) at 95° C. for 24 h. Purification by column chromatography (basic alumina, 0-30% EtOAc in hexanes) gave 1′-(5,7-difluoro-3-methyl-2-(4-methyl-2-pyridinyl)-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 8.60 (1H, d, J=5.1 Hz), 7.68-7.74 (2H, m), 7.54-7.58 (1H, m), 7.21-7.27 (1H, m), 7.02 (1H, t, J=3.1 Hz), 5.78 (1H, s), 4.14 (2H, td, J=11.6, 3.9 Hz), 3.92-4.00 (1H, m), 3.71-3.84 (5H, m), 3.49-3.62 (2H, m), 2.98-3.08 (4H, m), 2.51 (3H, s), 2.37-2.42 (3H, m), 1.83 (1H, d, J=13.9 Hz), 1.68-1.78 (1H, m), 1.28-1.34 (2H, m). Mass Spectrum (ESI) m/e=544.1 (M+1).
