Potassium Carbonate → HCID 67284990, compound

Participants

Reaction Steps

Freshly prepared powdered 3 Å molecular sieves were transferred to a round bottom flask and activated by heating under vacuum for 3 min. After this time the flask was allowed to cool to rt for 10 min. At this time, K2CO3 (601 mg, 4.35 mmol), 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-tri-i-propylbiphenyl (209 mg, 0.435 mmol), Pd2dba3 (199 mg, 0.217 mmol), 2,4-dichloro-7-fluoro-3-methylquinoline (500 mg, 2.173 mmol), delta-valerolactam (215 mg, 2.173 mmol) and the previously activated molecular sieves were suspended in tBuOH (4 mL) and heated in the microwave for 1 h at 150° C. After this time the reaction was partitioned between EtOAc (70 mL) and water (40 mL). The separated aqueous layer was extracted with EtOAc (40 mL) and the combined organic extracts were washed with water (20 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography (hexanes:EtOAc, 1:0 to 2:1) gave 1-(4-chloro-7-fluoro-3-methylquinolin-2-yl)piperidin-2-one. 1H NMR (400 MHz, chloroform-d) δ ppm 8.12-8.29 (1H, m), 7.63 (1H, dd, J=9.8, 2.5 Hz), 7.35-7.47 (1H, m), 4.07-4.22 (1H, m), 3.39-3.53 (1H, m), 2.54-2.70 (2H, m), 2.35-2.50 (3H, m), 1.90-2.15 (4H, m). Mass Spectrum (ESI) m/e=293.0 (M+1).

Provenance & Evidence