Cesium carbonate → HCID 118324000, compound

Participants

Reaction Conditions

Reaction Steps

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 6-[bis(4-chlorophenyl)methyl]-4-bromoquinolin-2-ol (300 mg, 0.65 mmol, 1.00 equip), tert-butyl 2-(4-aminophenoxy)acetate (220.8 mg, 0.98 mmol, 1.50 equip, 99%), Pd2(dba)3 (60 mg, 0.06 mmol, 0.10 equip, 99%), dppf (126.7 mg, 0.23 mmol, 0.35 equip, 99%), Cs2CO3 (532.7 mg, 1.62 mmol, 2.50 equip, 99%), and 1,4-dioxane (9 mL). The resulting solution was stirred overnight at 100° C. in an oil bath. The resulting solution was diluted with water (60 mL). The resulting solution was extracted with ethyl acetate (3×60 mL) and the organic layers combined. The resulting mixture was washed with water (1×60 mL) and brine (1×60 mL). The resulting mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (30:1). The resulting residue was recrystallized from EtOAc:n-hexane in the ratio of 1:20 to yield tert-butyl 2-(4-((6-(bis(4-chlorophenyl)methyl)-2-oxo-1,2-dihydroquinolin-4-yl)amino)phenoxy)acetate as a white solid.

Provenance & Evidence