Dimethyl Sulfoxide → HCID 86711870, compound

Participants

Reaction Conditions

Reaction Steps

1-Benzyl-4-bromo-3-(4-chlorophenyl)-N-(2,2-dimethylpropyl)-N-methyl-5-(trifluoromethyl)pyrrole-2-carboxamide (100 mg, 0.18 mmol) followed by SODIUM METHANESULFINATE (4.0 equiv., 0.078 g, 0.74 mmol), COPPER(I) TRIFLATE BENZENE COMPLEX (0.1 equiv., 0.010 g, 0.018 mmol), DIMETHYL SULFOXIDE (0.6 mL) and N,N′-DIMETHYLETHYLENEDIAMINE (0.2 equiv., 0.003 g, 0.037 mmol) added to reactivial. Flushed with Nitrogen and heated at 140° C. for 18 hours (overnight). Black solid residue formed. Work Up: Diluted with 50 ml Dichloromethane and 100 ml Water then filtered to remove solids. Dichloromethane/Water shaken and separated. Aqueous extracted 2×50 ml Dichloromethane. Organics combined and filtered through hydrophobic frit, then reduced under vacuum. Purification: Purified via Preparative HPLC over 2 injections using 50-95% acetonitrile/water (0.1% Formic Acid) over 15 minutes collecting at 254 nm. Pure fractions combined and reduced under vacuum to yield product as 51.4 mg (0.09 mmol) beige solid.

Provenance & Evidence