3-(4-Chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylic acid → 3-(4-Chlorophenyl)-1h-indol-4-yl methyl sulfide

Participants

Reaction Steps

To a solution of 1.4 g of the acid of Step 5 in quinoline (10 mL) was added 100 mg of copper powder. The reaction mixture was heated to reflux and stirred for 2 hours. The copper powder was removed by filtration and 6N HCl was added to the filtrate. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 10% EtOAc in Hexanes to provide 750 mg of the title compound as an orange solid foam.

Provenance & Evidence