Acetic Acid → HCID 86732760, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-ethyl-8-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carbaldehyde (6.5 g, 13.22 mmol) in 1,2-Dichloroethane (DCE) (100 mL) was added pyrrolidine (1.637 mL, 19.84 mmol), sodium triacetoxyborohydride (5.61 g, 26.4 mmol) and AcOH (0.076 mL, 1.322 mmol). The reaction mixture was stirred at 25° C. for 3 h. LCMS indicated completion of the reaction. The mixture was diluted with DCM and washed with brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The crude material was purified by normal phase automatic silica column chromatography (Combiflash RF, 40 g golden column) eluting with MeOH/DCM (0-20%), and purified again with reverse phase automatic silica column chromatography (Combiflash RF, 150 g golden column) eluting with acetonitrile/Water (0-60%) to afford 1-ethyl-8-fluoro-6,7-bis((4-methoxybenzyl)oxy)-3-(pyrrolidin-1-ylmethyl)quinolin-4(1H)-one (4.3 g, 7.87 mmol, 59.5% yield) as a pale yellow solid.

Provenance & Evidence