1-Phenylpiperazine → 2-Methyl-2-[(4-{2-[4-(4-phenylpiperazin-1-yl)phenoxy]ethyl}-1,3-thiazol-2-yl)thio]propionic acid tert-butyl ester

Participants

Reaction Steps

Under nitrogen atmosphere, 2-({4-[2-(4-bromophenoxy)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester (800 mg) synthesized in Example 67-1 and 1-phenylpiperazine (425 mg) were dissolved in toluene (5 mL), sodium tert-butoxide (185 mg), tris(dibenzylideneacetone)dipalladium (80.1 mg) and 2-(di-tert-butylphosphino)biphenyl (52.2 mg) were added, and the mixture was refluxed for 4 hr. The reaction mixture was cooled, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1) to give the title compound (490 mg) as a yellow oil.

Provenance & Evidence