5-Azaindole → HCID 57985923, compound

Participants

Reaction Conditions

Reaction Steps

To a RT solution of isopropylmagnesium chloride (1.5 M in THF, 2.4 mL, 3.6 mmol) in THF (10 mL) was added a solution of 1H-pyrrolo[3,2-c]pyridine (350 mg, 3 mmol) in THF (3 mL), followed by a solution of ZnCl2 in THF (1 M, 3.4 mL). After stirring the resulting mixture at 50° C. for 5 minutes, 2-benzylidene-malonic acid diethyl ester (1.0 mL, 4.5 mmol) was added dropwise. The mixture was stirred at 50° C. for 3 h, cooled to RT, quenched by addition of a saturated solution of NH4Cl, and extracted 3 times with EtOAc. The combined extracts were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (EtOAc), affording 2-[Phenyl-(1H-pyrrolo[3,2-c]pyridin-3-yl)-methyl]-malonic acid diethyl ester (0.77 g, 70% yield).

Provenance & Evidence