Potassium Carbonate → 3-(2,2-Dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-[5-(1-pyrrolidinylmethyl)-2-thienyl]-1H-indole-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

3-(2,2-Dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (75 mg, 0.17 mmol), 1-[(5-bromo-2-thienyl)methyl]pyrrolidine (50 mg, 0.17 mmol), PdCl2(dppf)-CH2Cl2 adduct (20 mg, 0.024 mmol), and potassium carbonate (100 mg, 0.72 mmol) were diluted in a mixture of 1,4-dioxane (3 mL) and water (1.5 mL) in a 2-5 mL microwave tube. The mixture was degassed by bubbling argon through for 5 minutes, then heated in a biotage microwave at 100° C. for 5 minutes. The crude reaction mixture was filtered through a thiol SPE cartridge (polymer labs) to remove palladium, and concentrated. The residue was dissolved in ˜3 mL of dmso, and filtered through a syringe filter. The crude product was purified by ammonium hydroxide Gilson HPLC, and the desired fractions were concentrated. The product was further purified by trituration from diethyl ether to afford 18.6 mg of the title compound.

Provenance & Evidence