6-Azaindole → HCID 57516335, compound

Participants

Reaction Steps

To a stirred solution of 1H-pyrrolo[2,3-c]pyridine (1 g, 8.46 mmol) in DMF (10 mL) under nitrogen atmosphere NaH (0.504 g, 12.6 mmol) is added in portions at ice-cold conditions. The reaction mixture is allowed to stir for 30 min at room temperature. It is then cooled in an ice-bath and bromoacetic acid benzyl ester (1.46 mL, 9.31 mmol) in DMF (10 mL) is added dropwise. The reaction mixture is stirred at room temperature for 5 h. Saturated aqueous NH4Cl solution is added to quench the reaction mixture at ice-cold conditions, then diluted with water (200 mL) and extracted with EtOAc (3×100 mL). Combined organic layer is washed with water followed by brine. It is then dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography (silica-gel, 100-200 mesh, eluent; EtOAc to 2% MeOH in EtOAc) to afford pyrrolo[2,3-c]pyridin-1-yl-acetic acid benzyl ester (1.4 g) as a solid.

Provenance & Evidence