Dimethyl Sulfoxide → HCID 136367318, compound

Participants

Reaction Conditions

Reaction Steps

A dry flask is charged with 0.399 mL oxalyl chloride and 69 mL dichloromethane. After cooling to −78° C. 0.304 mL DMSO is added dropwise. After stirring for 15 minutes at this temperature, 2.04 g (6-hydroxymethyl-2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester in 46 mL dichloromethane are slowly added by syringe. After stirring for 60 minutes at −78° C. 2.98 mL triethylamine is added. The reaction mixture is stirred for 60 minutes at −78° C., allowed to warm to 0° C. and quenched by addition of sat. aq. NH4Cl-solution. The reaction mixture is diluted with dichloromethane, washed with sat. aq. NH4Cl-solution and brine, dried (MgSO4) and concentrated in vacuo. 1.96 g (97%) crude 6-formyl-2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester are obtained.

Provenance & Evidence