Cesium carbonate → HCID 178516448, compound

Participants

Reaction Conditions

Reaction Steps

Into a 8-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 6-[bis(4-chlorophenyl)methyl]-4-bromoquinolin-2-ol (200 mg, 0.44 mmol, 1.00 equip), 1,4-dioxane (5 mL), 1-(2,2,2-trifluoroethyl)piperidin-4-amine 2,2,2-trifluoroacetate (193 mg, 0.65 mmol, 1.50 equip), Pd2(dba)3 (40 mg, 0.04 mmol, 0.10 equip), dppf (84.5 mg, 0.15 mmol, 0.35 equip), Cs2CO3 (355 mg, 1.09 mmol, 2.50 equip), and KOt-Bu (97.6 mg, 0.87 mmol, 2.00 equip). The resulting solution was stirred overnight at 100° C. The reaction was then quenched by the addition of water (100 mL). The resulting solution was extracted with ethyl acetate (3×50 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were removed by filtration. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (20:1). The resulting residue was recrystallized from ethyl acetate:petroleum ether in the ratio of 1:10 to yield 6-[bis(4-chlorophenyl)methyl]-4-[[1-(2,2,2-trifluoroethyl)piperidin-4-yl]amino]quinolin-2-ol as a white solid.

Provenance & Evidence