Dimethylformamide → 1H-Pyrrolo(2,3-b)pyridine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of bromide 24 (10.0 g, 50.8 mmol), ZnCl2 (3.58 g, 30.5 mmol), and Pd(PPh3)4 (3.52 g, 3.05 mmol) in DMF (110 mL) was heated at 80° C. overnight. The solvent was evaporated and the residue separated by silicagel chromatography (100 g column) using hexane:ethyl acetate as eluent (gradient elution). The resulting solid was partitioned between water (200 mL)/CH2Cl2 (100 mL) and the aqueous phase extracted with more CH2Cl2 (4×100 mL). The combined organic extracts were dried (MgSO4) and concentrated to give the product as a white solid (5.48 g, 75%), which was used for subsequent reactions without further purification.

Provenance & Evidence