ethyl 3-(1H-indol-3-yl)butanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5 g ethyl 3-(3-indolyl)-butyrate and 1.15 ml of 3-bromopyridine in 25 ml of pyridine is refluxed with 1.25 g of copper oxide and 1.25 g of potassium carbonate for 72 hours, filtered and evaporated to a brown oil which is chromatographed on 64 g of silica with 8:1 toluene-ethyl acetate to yield 3-(3-ethoxycarbonyl-2-propyl)-N-(3-pyridyl)indole; Rf (15% EtOAc, 85% toluene/silica gel)=0.35; IR (CH2Cl2) 1725 cm-1. filtered evaporated to a brown oil which is chromatographed on 64 g of silica with 8:1 toluene-ethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5 g ethyl 3-(3-indolyl)-butyrate and 1.15 ml of 3-bromopyridine in 25 ml of pyridine is refluxed with 1.25 g of copper oxide and 1.25 g of potassium carbonate for 72 hours, filtered and evaporated to a brown oil which is chromatographed on 64 g of silica with 8:1 toluene-ethyl acetate to yield 3-(3-ethoxycarbonyl-2-propyl)-N-(3-pyridyl)indole; Rf (15% EtOAc, 85% toluene/silica gel)=0.35; IR (CH2Cl2) 1725 cm-1. filtered evaporated to a brown oil which is chromatographed on 64 g of silica with 8:1 toluene-ethyl acetate