Potassium Carbonate → HCID 59332719, compound

Participants

Reaction Conditions

Reaction Steps

5-bromo-3-(2,6-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (0.050 g, 0.125 mmol) and 3-thienylboronic acid (0.016 g, 0.125 mmol) 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 (0.087 g, 0.626 mmol, 5 eq) was added and the solution was degassed with Nitrogen. PdCl2(dppf)2 (0.016 g, 0.021 mmol, 0.17 eq) 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% TFA. The desired fractions were concentrated, giving 0.051 g of a mixture of diasteriomers and their respective enantiomers.

Provenance & Evidence