Sodium t-butoxide → 1-(7-fluoro-3-methyl-4-(6'-(4-morpholinyl)-2,3,5,6-tetrahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridin]-1'(2'H)-yl)-2-quinolinyl)-2-pyrrolidinone

Participants

Reaction Steps

Prepared according to procedure Y by stirring 1-(4-chloro-7-fluoro-3-methylquinolin-2-yl)pyrrolidin-2-one (50 mg, 0.179 mmol), 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (49.4 mg, 0.179 mmol), XPhos precatalyst (26.5 mg, 0.036 mmol), sodium tert-butoxide (34.5 mg, 0.359 mmol), and toluene (1.5 mL) at 95° C. for 2 h. Purification by reverse phase HPLC (0-70% acetonitrile in water) gave 1-(7-fluoro-3-methyl-4-(6′-(4-morpholinyl)-2,3,5,6-tetrahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridin]-1′(2′H)-yl)-2-quinolinyl)-2-pyrrolidinone. 1H NMR (400 MHz, chloroform-d) δ ppm 7.76 (1H, dd, J=9.1, 6.0 Hz), 7.61-7.69 (2H, m), 7.21-7.26 (1H, m), 5.89 (1H, s), 4.13 (4H, d, J=6.8 Hz), 4.04-4.10 (1H, m), 3.93 (1H, d, J=9.6 Hz), 3.70-3.83 (4H, m), 3.51-3.66 (2H, m), 3.03 (4H, dd, J=5.7, 3.7 Hz), 2.65 (2H, t, J=8.0 Hz), 2.24-2.42 (4H, m), 2.18 (3H, s), 1.83 (1H, d, J=13.7 Hz), 1.73 (1H, d, J=13.3 Hz). Mass Spectrum (ESI) m/e=518.2 (M+1).

Provenance & Evidence