Sodium t-butoxide → HCID 67285432, compound

Participants

Reaction Steps

Prepared according to procedure Y by using 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-2,2-dimethylmorpholine (47.5 mg, 0.14 mmol), 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (40 mg, 0.14 mmol), sodium tert-butoxide and XPhos precatalyst (10.7 mg, 0.01 mmol) in toluene (4 mL) for 2 h at reflux. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 1′-(2-(2,2-dimethyl-4-morpholinyl)-5,7-difluoro-3-methyl-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 7.57 (1H, d, J=2.5 Hz), 7.35-7.40 (1H, m), 6.75 (1H, ddd, J=11.8, 8.9, 2.5 Hz), 5.67 (1H, d, J=2.3 Hz), 4.09-4.18 (2H, m), 3.94-4.00 (2H, m), 3.82-3.94 (2H, m), 3.72-3.80 (4H, m), 3.51-3.63 (2H, m), 3.27-3.38 (2H, m), 3.11-3.25 (2H, m), 2.95-3.02 (4H, m), 2.23-2.38 (5H, m), 1.55-1.78 (2H, m), 1.40 (3H, s), 1.37 (3H, s). Mass Spectrum (ESI) m/e=566.2 (M+1).

Provenance & Evidence