Bromine → HCID 89876355, compound

Participants

Reaction Steps

Part of a solution of bromine (200 mg, 1.25 mmol) in DCM (4 mL) is added dropwise, slowly, to a solution of 4-(3-chloroindol-1-yl)-5-methoxy-2,6-dimethyl-pyridazin-3-one (184 mg, 0.606 mmol) in DCM (2 mL) at 0° C. The bromine decolourised as it was added and addition was continued cautiously until an orange colour just persisted. NaHCO3 (0.5 g saturated solution in water) is added cautiously, followed by sufficient sodium metabisulphite to decolorise the excess bromine. The resulting reaction mixture was extracted with DCM (3×60 mL) and the combined DCM layers were filtered through MgSO4 and concentrated in vacuo. The resulting yellow gum was purified by flash chromatography (combiflash, 0 to 30% DCM/EtOAc) to yield the desired pro duct 5-methoxy-2,6-dimethyl-4-(2-bromo-3-chloroindol-1-yl)pyridazin-3-one (115 mg, 0.301 mmol, 50% Yield) as a white solid.

Provenance & Evidence