Trimethylsilylacetylene → HCID 57809256, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 5-dimethylsulfamoyl-2-ethoxy-4-iodobenzoate (0.142 g, 0.332 mmol; prepared as described in example 14), dichlorobis(triphenylphosphine)palladium(II) (0.023 g, 0.032 mmol), copper(II) iodide (3.2 mg, 0.017 mmol) dimethylformamide (0.5 mL), triethylamine (0.5 mL) and (trimethylsilyl)acetylene (0.066 mL, 0.47 mmol) were added sequentially to a flame-dried Schienk tube. The reaction mixture was heated at 50° C. oil bath for 2 h, allowed to cool to room temperature overnight and then partitioned between water (20 mL) and diethyl ether (3×20 mL), dried over magnesium sulfate and evaporated. The residue was purified by flash column chromatography (eluting with 20% ethyl acetate in hexanes) to give ethyl 5-dimethylsulfamoyl-2-ethoxy-4-trimethylsilanylethynylbenzoate as an off-white glass (0.111 g, 84%). LC-MS: 398.3 [(M+H)+].

Provenance & Evidence