Sodium t-butoxide → HCID 67285558, compound

Participants

Reaction Steps

Prepared according to procedure Y by stirring 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (56.4 mg, 0.20 mmol), 1-(4-chloro-7-fluoro-3-methylquinolin-2-yl)piperidin-2-one (60 mg, 0.20 mmol), sodium tert-butoxide (39.4 mg, 0.41 mmol) and XPhos precatalyst (15.1 mg, 0.020 mmol) in toluene (1.5 mL) at 130° C. for 1 h and 15 min in a microwave reactor. Purification by column chromatography (DCM: (DCM:MeOH:NH4OH, 9:1:0.4) from 1:0 to 7:3) gave the desired product. Further purification by reverse phase HPLC (10 to 60% 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-piperidinone. 1H NMR (500 MHz, chloroform-d) δ ppm 7.59-7.84 (3H, m), 7.20-7.33 (1H, m), 6.02-5.69 (1H, m), 4.10-4.34 (3H, m), 3.88-4.08 (1H, m), 3.71-3.82 (4H, m), 3.41-3.64 (4H, m), 2.91-3.15 (4H, m), 2.53-2.68 (2H, m), 2.28-2.41 (2H, m), 1.98-2.18 (7H, m), 1.78-1.87 (2H, m). Mass Spectrum (ESI) m/e=532.2 (M+1).

Provenance & Evidence