(R)-tert-Butyl 2-(5-bromo-1-methyl-1H-indol-2-yl)pyrrolidine-1-carboxylate (0.300 g, 0.79 mmol), bis(pinacolato) diborate (0.240 g, 0.95 mmol), Pd(OAc)2 (6.0 mg, 0.03 mmol, 3.5 mol %), Ru-Phos ligand (26.0 mg, 0.06 mmol, 7 mol %) and KOAc (0.240 g, 2.44 mmol) were mixed together in a vial. The vial was vacuumed and backfilled with argon before dioxane (2 mL) was added. Mixture was heated at 100° C. for ˜3 h until complete consumption of the starting bromide was observed. Reaction mixture was cooled to room temperature before H2O (0.90 mL), K2CO3 (0.330 g, 2.39 mmol) and 6-chloro-5-ethyl-2-methoxynicotinate (0.182 g, 0.79 mmol) were added. Reaction vial was resealed under argon and mixture was heated at 100° C. overnight and then cooled to room temperature. Water (7 mL) was added to the reaction mixture and product was extracted with DCM (2×10 mL). Combined organics were washed with NaCl (aqueous saturated, 10 mL) and dried over Na2SO4. Upon concentration of the solvent residue was purified by column chromatography (EtOAc/hexanes, 0-50% gradient) to afford product as solid (0.192 g) in 49% overall yield.
