6-Azaindole → HCID 57985922, compound

Participants

Reaction Steps

To a RT solution of 1H-pyrrolo[2,3-c]pyridine (595 mg, 5.04 mmol) in THF (20 mL) was added i-PrMgCl (1.5 M in THF, 5.0 mL, 7.6 mmol) followed by ZnCl2 (1M in Et2O, 7.6 mL). The resulting mixture was stirred at RT for 5 min then a solution of 2-benzylidene-malonic acid diethyl ester (2.2 mL, 10 mmol) in THF (20 mL) was added dropwise. The mixture was stirred at RT for 1 hour, quenched by addition of a saturated solution of NH4Cl, and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH/NH4OH), affording 2-[Phenyl-(1H-pyrrolo[2,3-c]pyridin-3-yl)-methyl]-malonic acid diethyl ester (0.33 g, 18% yield).

Provenance & Evidence