Triethylamine → 5-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole-2,3-dione

Participants

Reaction Steps

A mixture of 4-benzyl-1-(3-butynyl)piperidine (904 mg, 4 mmol), Et3N (4 mL), CuI (76 mg, 0.4 mmol) and Pd(PPh3)2Cl2 (41 mg, 0.1 mmol) in DMF (10 mL) is stirred at room temperature under N2 for 30 min. 5-Iodoisatin (546 mg, 2 mmol) is added and stirring continued overnight. The mixture is evaporated and the residue purified by medium-pressure column chromatography on silica gel eluting with 50% EtOAc/hexanes (+1% Et3N) to give an orange solid (238 mg). The solid is recrystallized from hot 90:10 isopropanol:water to give the title compound as orange crystals (152 mg): mp 140-141° C.

Provenance & Evidence