Indole → HCID 85665195, compound

Participants

Reaction Steps

The title C indole (1.001 g, 5.713 mmol, 1.0 eq.) was dissolved in pyridine (11.4 ml, 0.5M) and treated with 4-bromotoluene (1.76 ml, 22.85 mmol, 4 eq.) and copper(I) oxide (1.635 g, 11.43 mmol, 2.0 eq.). The mixture was heated in a bath maintained at 130°±5° C. for a total of nine hours. During this period, at 3, 5.5 and 7.5 hours, additional 4-bromotoluene (0.44 ml, 5.71 mmol, 1 eq.) and copper(I) oxide (409 mg, 2.85 mmol, 0.5 eq.) were added. After cooling, the mixture was diluted with ethyl acetate (~10 ml) and filtered through Celite. The filtrate was washed with water (3×50 ml), 0.5N hydrochloric acid (2×50 ml), 1.0N hydrochloric acid (50 ml) and saturated sodium hydrogen carbonate solution. The organic solution was dried over anhydrous magnesium sulfate and freed of solvent in vacuo. The remaining material was first chromatographed on silica gel, eluting with 5% ether in hexane to give a mixture of the desired product and starting material but free of the large amount of excess 4-bromotoluene. The mixture was then rechromatographed on silica gel, eluting with 3% acetone in hexane to give the title D compound (467 mg).

Provenance & Evidence