Water → 4-Cyano-2-{5-[4-(6-{2-[1-(2-methoxycarbonylamino-3-methyl-butyryl)-4-methylene-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

(1-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-4-methylene-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (202 mg, 0.392 mmol), 4-Cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (181 mg, 0.392 mmol), Pd[PPh3] (45.6 mg, 0.0392 mmol), potassium carbonate (108 mg, 0.784 mmol) were heated in DME (3 mL)/water (0.4 mL) at 120° C. for 20 minutes under microwave conditions. The volatiles were removed in vacuo and the crude was partitioned between EtOAc and brine/aqueous sodium bicarbonate solution. The organic layer was dried over sodium sulfate. Filtration and evaporation of solvents yielded the crude material, which was purified via flash chromatography on silica gel to yield the product. (161 mg).

Provenance & Evidence