Dichloromethane → HCID 178502118, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (2S,4S)-4-methyl-2{-4-[4′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (211 mg, 0.3985 mmol), methyl N-[1-[(2S,4S)-2-(5-iodo-1H-benzimidazol-2-yl)-4-methyl-pyrrolidine-1-carbonyl]-2-methyl-propyl]-N-methyl-carbamate (198.6 mg, 0.3985 mmol), Pd(DPPF)(Cl)2.CH2Cl2 (32.54 mg, 0.03985 mmol) in 2-propnaol (2.1 mL) is added 1M aqueous NaHCO3 (2 mL, 2 mmol). The reaction mixture is stirred at 80° C. for 18 hours, cooled to RT, filtered on a bed of Celite and concentrated to dryness. The residue is purified by flash column chromatography on silica gel (12 to 100% EtOAc in hexanes) to give 2S,4S)-2-{4-[4′-(2-{(2S,4S)-1-[(S)-2-(methoxycarbonyl-methyl-amino)-3-methyl-butyryl]-4-methyl-pyrrolidin-2-yl}-1H-benzoimidazol-5-yl)-biphenyl-4-yl]-1H-imidazol-2-yl}-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (115 mg, 37%).

Provenance & Evidence