Hydrochloric Acid → HCID 57543456, compound

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)2Cl2 (153 mg, 0.22 mmol) and copper(I)iodide (42 mg, 0.22 mmol) were dissolved in triethylamine (40 ml) and refluxed under argon for 20 min. The reaction mixture was then cooled down to 0° C. and (4-chloro-5-fluoro-2-iodo-phenyl)-carbamic acid methyl ester (7.2 g, 21 mmol) was added. After 10 min stirring at rt, ethinyltrimethylsilane (3.45 ml, 24.9 mmol) was added dropwise (exothermic, temperature raises from 18 to 33° C.) and the reaction mixture was stirred for one hour at rt. The reaction mixture was then poured on 1N aq. HCl solution (180 ml) and ice and extracted twice with ethyl acetate (180 ml). The combined organic phases were washed with water and sat. aq. NaCl solution, dried over magnesium sulfate, filtered and concentrated in vacuo to yield crude (4-chloro-5-fluoro-2-trimethylsilanylethynyl-phenyl)-carbamic acid methyl ester.

Provenance & Evidence