Sodium Carbonate → HCID 53246857, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of phenylboronic acid (26.9 mg, 0.221 mmol) in methanol (1.0 mL) and toluene (1.0 mL) was added ethyl 2-(3-iodo-2,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)phenylthio)-1H-pyrrol-1-yl)acetate (121 mg, 0.221 mmol), palladium tetrakistriphenylphosphine (12.8 mg, 0.0110 mmol) and sodium carbonate (0.090 mL, 0.18 mmol). The reaction mixture was heated at 100° C. for 2.5 hours, then heated at 60° C. for 16 hours, after which an additional 0.10 equiv. of both phenylboronic acid and palladium tetrakistriphenylphosphine were added. The reaction was then heated at 100° C. for one more hour, after which it was allowed to cool down to room temperature, poured over ice water (10 mL), extracted with ether (2×20 mL), and washed with water (1×30 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated. Purification by column chromatography on silica gel afforded methyl 2-(2,5-dimethyl-3-phenyl-4-(2-(pyrrolidin-1-ylsulfonyl)phenylthio)-1H-pyrrol-1-yl)acetate (0.0246 g, 0.0510 mmol, 23% yield) as a light brown residue. LCMS: ES+ [M+H]+=485.3

Provenance & Evidence