Hydrochloric Acid → 5-Cyano-2,3-dimethyl-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

An autoclave was charged with 5-bromo-2,3-dimethyl-pyrrolo[2,3-b]pyridine (prepared in a similar manner as 6-bromo-2,3-dimethyl-pyrrolo[2,3-b]pyridine (247 mg, 1.1 mmol) and CuCN (135 mg. 1.5 mmol). The mixture was covered with pyridine and heated to 220° C. for 12 h. After cooling the raction mixture was poured into a mixture of FeCl3 hexahydrate (0.9 g), conc HCl (0.5 ml), and water (10 ml). The mixture was heated to 80° C. for 1 h and extracted with CH2Cl2. The organic layer was washed four times with 2M HCl, dried over MgSO4 and evaporated leaving 77 mg (40%) 5-cyano-2,3-dimethyl-pyrrolo[2,3-b]pyridine.

Provenance & Evidence