Potassium Carbonate → HCID 86708757, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl (S)-1-((S)-2-(5-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (466 mg, 0.77 mmol), bis(pinacolato)diboron (235 mg, 0.93 mmol) and potassium acetate (227 mg, 2.3 mmol) in dioxane (4 mL) was degassed with a stream of argon for fifteen minutes. To this mixture was added PdCl2(dppf) (56 mg, 0.08 mmol) and the reaction was heated to 90° C. After 14 hours, the mixture was cooled to room temperature. To the reaction was added (S)-tert-butyl 2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (341 mg, 1.1 mmol), 2M aqueous potassium carbonate solution (1.54 mL, 3.1 mmol) and DMSO (3.9 mL). The reaction was degassed with a stream of argon for fifteen minutes. Tetrakis(triphenylphosphine)palladium(0) (89 mg, 0.08 mmol) was added and the reaction was heated to 90° C. After 4.5 hours, the reaction was poured into water. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The crude material was purified by flash column chromatography to yield (S)-tert-butyl 2-(5-(2-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)-6H-dibenzo[c,h]-chromen-8-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (145 mg, 25%).

Provenance & Evidence