Dimethylformamide → HCID 50939865, compound

Participants

Reaction Steps

Under a N2 atmosphere, 3,3-dimethyl-6-morpholinoindoline (0.100 g, 0.430 mmol) was dissolved in DMF (2.00 mL, 26.0 mmol). Sodium hydride (0.0227 g, 0.947 mmol) was added and the reaction was stirred at rt for 12 minutes. The reaction was treated with 4-chloro-3-methyl-2-phenylquinoline (0.218 g, 0.861 mmol) and placed in a preheated oil bath at 140° C. for 2 h. LCMS showed no starting quinoline remained. The reaction was diluted with EtOAc and 2% sodium bicarbonate. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography eluting with 20% to 50% EtOAc in hexane, and then purified again by preparative reverse phase chromatography to give 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-3-methyl-2-phenylquinoline. Mass Spectrum (ESI) m/e=450.2 (M+1)

Provenance & Evidence