Water → (R)-3-[5-Cyano-1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-3-(5-cyano-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl ester (60 mg, 0.18 mmol) in DMF (5 ml) were added (1,4-dimethyl-1H-indol-3-ylmethyl)-trimethyl-ammonium iodide (74 mg, 0.21 mmol) and K2CO3 (30 mg, 0.21 mmol) at room temperature under nitrogen atmosphere. The solution was heated at 60° C. for 18 hours. The solution was cooled and poured into water and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (1×). The combined organics were dried (MgSO4), filtered and concentrated. The remaining residue was purified via silica gel flash column chromatography (Companion, 12 g silica gel, 30-50% EtOAc/hexanes) to give 70 mg (80%) of the title compound as foam.

Provenance & Evidence