Ammonium fluoride → 4-Chloro-5-(2-furyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone

Participants

Reaction Conditions

Reaction Steps

4-Chloro-5-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (100 mg, 0.159 mmol) was dissolved in 1,4-dioxane (3.0 mL), and the solution was added with 2-(tributylstannyl)furan (0.150 mL, 0.477 mmol), tetrakis(triphenylphosphine)palladium (15.0 mg, 0.0130 mmol) and lithium chloride (60.6 mg, 1.43 mmol), followed by stirring at 90° C. for 6.0 hours under argon atmosphere. The reaction mixture was added with 10% aqueous ammonium fluoride solution and filtered using Celite. The filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=6/1) to obtain 4-chloro-5-(2-furyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (52.2 mg, yield 60%).

Provenance & Evidence