Reaction Steps
A mixture of 2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (26.9 mg, 0.056 mmol), Pd2dba3 (25.9 mg, 0.028 mmol), sodium tert-butoxide (45.4 mg, 0.47 mmol), 6-morpholino-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (50 mg, 0.18 mmol) (described herein), and 4-chloro-7-fluoro-2-(6-methoxypyridin-2-yl)-3-methylquinoline (57 mg, 0.19 mmol) (described herein) in toluene (2 mL) was stirred at 100° C. for 18 h, then cooled to rt and concentrated. The resulting residue was taken up in EtOAc, washed with saturated aqueous sodium bicarbonate solution, 1 M NaOH, and brine, and the organic layer dried (MgSO4) and concentrated. Column chromatography afforded 1-(7-fluoro-2-(6-methoxy-2-pyridinyl)-3-methyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran] as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.75-7.90 (3H, m), 7.55 (1H, dd, J=7.2, 0.8 Hz), 7.22-7.27 (1H, m), 7.11-7.19 (1H, m), 6.85 (1H, dd, J=8.3, 0.9 Hz), 6.30-6.39 (1H, m), 5.64 (1H, d, J=2.2 Hz), 3.93-4.09 (7H, m), 3.67-3.79 (4H, m), 3.48-3.64 (2H, m), 2.91-3.05 (4H, m), 2.39-2.48 (3H, m), 2.09-2.24 (2H, m), 1.90 (1H, dt, J=13.8, 1.1 Hz), 1.76-1.86 (1H, m). Mass Spectrum (ESI) m/e=541 (M+1).
