5-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-nicotinic acid methyl ester (0.100 g, 0.3 mmol), 4-bromo-1-methyl-1H-pyrazole (0.0966 mL, 0.9 mmol), copper(II) oxide (0.048 g, 0.6 mmol) and potassium carbonate (0.054 g, 0.39 mmol) were combined in pyridine (1 mL) in a sealed vial. The reaction was heated to 150° C. overnight then cooled, then diluted with EtOAc. The mixture was washed with HCl (1 M aq.) and brine, and the organic portion was dried and concentrated to yield the title compound as a crude mixture that was used directly in the next step.
