Iodine → HCID 89876160, compound

Participants

Reaction Steps

To a stirred solution of 5-(2,3-dichloroindol-1-yl)-4-methoxy-1-methyl-6-oxo-pyridazine-3-carbaldehyde (98 mg, 0.278 mmol) in THF (1.5 mL) is added ammonium hydroxide (30% aq. solution, 1.5 mL), followed by iodine (92 mg, 0.362 mmol), which caused a dark brown colour to appear. The resulting reaction mixture was stirred for 1 h and then quenched with NaHCO3 solution (5 mL) and Na2S2O3 solution (5 mL). This caused the reaction to change from dark brown to a clear pale yellow mixture. After stirring for 10 min the reaction was extracted with DCM (20 mL×2), dried (MgSO4) and concentrated under reduced pressure to afford the desired pro duct 5-(2,3-dichloroindol-1-yl)-4-methoxy-1-methyl-6-oxo-pyridazine-3-carbonitrile (82 mg, 0.235 mmol, 85%) as a yellow foam that crushed into a yellow solid.

Provenance & Evidence