Acetic Acid → HCID 86732809, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-ethyl-5-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carbaldehyde (18 g, 36.6 mmol) in 1,2-Dichloroethane (DCE) (100 mL) was added pyrrolidine (4.53 mL, 54.9 mmol), sodium triacetoxyborohydride (15.52 g, 73.2 mmol) and AcOH (0.105 mL, 1.831 mmol). The reaction mixture was stirred at 25° C. for 3 h. LCMS indicated completion of the reaction. The mixture was extracted with DCM and washed with brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude material was purified by normal phase automatic silica column chromatography (Combinflash RF), using a 40 g gold column and eluting with MeOH/DCM (0-20%). The product was further purified by reverse phase automatic chromatography (Combinflash RF), using a 150 g gold C18 column and eluting with acetonitrile/Water (0%-60%) to afford 1-ethyl-5-fluoro-6,7-bis((4-methoxybenzyl)oxy)-3-(pyrrolidin-1-ylmethyl)quinolin-4(1H)-one (9.4 g, 17.20 mmol, 47.0% yield) as a pale yellow solid. LCMS: (M+H)+: 547.3.

Provenance & Evidence