Thionyl Chloride → HCID 86700713, compound

Participants

Reaction Steps

Thionyl chloride (0.092 mL; 0.150 mmol) was added to a suspension of 6-chloropyridazine-3-carboxylic acid (0.100 g; 0.630 mmol) in chloroform (1 mL); the resulting mixture was refluxed for 18 hours and concentrated under reduced pressure. The residue was dissolved in dichloromethane (3 mL) and 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.160 g; 0.693 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.271 mL; 1.58 mmol) were added. The resulting green solution was stirred at room temperature for 2 hours, diluted with dichloromethane and successively washed with sodium hydrogen sulphate (1M), sodium carbonate (1M) and brine, dried over magnesium sulphate and the crude material was purified by flash chromatography on silica gel (eluent 10 to 60% ethyl acetate in dichloromethane) to yield 0.048 g (23%) of 6-chloro-N-(2-(5-chloro-1H-indol-3-yl)ethyl)pyridazine-3-carboxamide.

Provenance & Evidence