Dimethylamine → 1-(3-(N,N-dimethylamino)propyl)-6-(3-thienyl)-1H-indazole

Participants

Reaction Steps

A mixture of 1-(3-chloropropyl)-6-(3-thienyl)-1H-indazole (27.8 mg, 0.10 mmol), potassium iodide (155 mg, 1 mmol), potassium carbonate (130 mg, 1 mmol), and dimethylamine (2M in THF, 0.5 mL, 1 mmol) in acetonitrile (0.5 mL) was heated at reflux overnight. After cooling to room temperature, the mixture was diluted with dichloromethane (5 mL) and filtered through a small plug of alumina to remove the solids, rinsing with dichloromethane (10 mL). After removal of the solvent in vacuo, flash chromatography (silica gel, 2.5-5% 2M methanolic ammonia in dichloromethane) yielded 1-(3-(N,N-dimethylamino)propyl)-6-(3-thienyl)-1H-indazole (27.2 mg, 95%).

Provenance & Evidence