Potassium Carbonate → HCID 59631205, compound

Participants

Reaction Conditions

Reaction Steps

The piperazin-2-one (161 mg, 1.613 mmol) and 2,4-dichloro-5,7-difluoro-3-methylquinoline (400.0 mg, 1.613 mmol) were dissolved in t-BuOH (7.00 mL) and heated in the microwave at 100° C. for 30 min. Only a trace amount of product present. Potassium carbonate (557 mg, 4.03 mmol) was added and the mixture heated in the microwave at 100° C. for 45 min. Again, only a trace amount of product was observed. The 2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (123 mg, 0.258 mmol) and Pd2(dba)3 (59.1 mg, 0.065 mmol) was then added and the mixture was stirred in the microwave at 120° C. for 4 h. The reaction was then diluted with water (˜50 mL) and the mixture was extracted with EtOAc (1×100 mL), DCM (1×100 mL) and 10% MeOH:DCM (1×100 mL). The combined organic layers were dried over magnesium sulfate and the crude product was purified by medium pressure chromatography (silica, 0 to 10% 2M ammonia in MeOH:DCM) to give 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazin-2-one. Mass Spectrum (ESI) m/e=312.1 (M+1).

Provenance & Evidence