Sodium t-butoxide → 1'-(2-(3-Fluorophenyl)-3-methyl-1,8-naphthyridin-4-yl)-6'-(4-morpholinyl)-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Participants

Reaction Steps

Prepared according to procedure Y using 4-chloro-2-(3-fluorophenyl)-3-methyl-1,8-naphthyridine (49.5 mg, 0.182 mmol), 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (50 mg, 0.182 mmol), sodium tert-butoxide (34.9 mg, 0.363 mmol) and XPhos precatalyst (13.35 mg, 0.018 mmol) in toluene (4 mL) for 2 hours at 110° C. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 1′-(2-(3-fluorophenyl)-3-methyl-1,8-naphthyridin-4-yl)-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 9.13 (1H, dd, J=4.3, 2.0 Hz), 8.13 (1H, dd, J=8.2, 2.0 Hz), 7.66 (1H, d, J=2.3 Hz), 7.42-7.54 (4H, m), 7.15-7.23 (1H, m), 5.79 (1H, d, J=2.3 Hz), 4.14-4.21 (2H, m), 3.71-3.82 (4H, m), 3.56-3.65 (2H, m), 2.95-3.06 (4H, m), 2.30-2.43 (5H, m), 1.62-1.89 (4H, m). Mass Spectrum (ESI) m/e=512.2 (M+1).

Provenance & Evidence