Diisopropylamine → HCID 136399883, compound

Participants

Reaction Steps

A mixture of 7-bromo-3-(4-chloro-phenyl)-4-hydroxy-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (150 mg, 0.38 mmol), tris(dibenzylideneacetone)dipalladium(0) (27 mg, 0.04 mmol), copper (I) iodide (14 mg, 0.08 mmol), trimethylsilylacetylene (107 μl, 0.76 mmol), diisopropylamine (321 μl, 2.27 mmol), and tetrahydrofuran (3.8 ml) was refluxed for eighteen hours before it was cooled to room temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of hexanes and dichloromethane to give the title compound as a yellow solid (55 mg); MS (m/z): 415.34 (M+H+); 413.37 (M−H+).

Provenance & Evidence