Potassium Carbonate → 3-(1,1-Dioxidotetrahydro-2H-thiopyran-3-yl)-5-(3-furanyl)-1H-indole-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxamide (0.050 g, 0.135 mmol) and 3-furanylboronic acid (0.020 g, 0.175 mmol, 1.3 eq) was dissolved in a 6:1 solution of 1,4 dioxane (3 mL)/water (0.5 mL) in a 20 mL microwave reaction vessel. Potassium carbonate (0.093 g, 0.673 mmol, 5 eq) was added and the solution was degassed with Nitrogen. PdCl2(dppf)2 (0.017 g, 0.023 mmol) was added and the reaction was heated in a microwave at 100° C. for 20 min. The solution was passed through a StratoSphere SPE PL-Thiol MP SPE column to remove palladium and purified on Gilson preparative HPLC using Acetonitrile/Water with 0.1% NH4OH. The desired fractions were concentrated, giving 0.022 g (45%) of the title compound.

Provenance & Evidence