Dimethylformamide → HCID 89876203, compound

Participants

Reaction Steps

To a stirred solution of 4-(2,3-dichloroindol-1-yl)-6-(1-hydroxyethyl)-5-methoxy-2-methyl-pyridazin-3-one (98 mg, 0.27 mmol) in DMF (1 mL) at 0° C. is added sodium hydride (60% dispersion in mineral oil, 32 mg, 0.80 mmol). After stirring for 5 min, MeI (50 μL, 0.80 mmol) is added. After 30 min, the reaction is cautiously quenched with ammonium chloride solution (10 mL) and allowed to stand overnight. The following day, the reaction mixture is extracted with DCM (10 mL×3), then dried (MgSO4) and concentrated under reduced pressure. The residue is resubmitted to the reaction conditions with the same procedure and reagent/solvent quantities as above. After stirring for 30 min, it is warmed to RT and allowed to stir for a further 1.5 h. It is then cooled to 0° C. and then quenched cautiously with ammonium chloride solution (20 mL). Et2O is then added and the layers were separated. The organic layer is washed with water (20 mL×3), then dried (MgSO4) and concentrated under reduced pressure onto silica. Chromatography (0 to 30% EtOAc/isohexane) affords the desired product 4-(2,3-dichloroindol-1-yl)-5-methoxy-6-(1-methoxyethyl)-2-methyl-pyridazin-3-one (64 mg, 0.168 mmol, 63%) as a colourless oil.

Provenance & Evidence