2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl → 2-(4-((2S)-2-methyl-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-3,3,3-trifluoro-1,2-propanediol

Participants

Reaction Conditions

Reaction Steps

2-(4-bromophenyl)-3,3,3-trifluoro-1,2-propanediol (0.35 g, 1.2 mmol), (3S)-3-methyl-1-(2-thiophenylsulfonyl)piperazine (0.20 g, 0.81 mmol), sodium tert-butoxide (0.27 g, 2.8 mmol), dicyclohexyl(2′,6′-diisopropoxybiphenyl-2-yl)phosphine (RuPhos) (0.076 g, 0.16 mmol, Strem Chemical Inc, Newburyport, Mass.), tris(dibenzylideneacetone)dipalladium (0) (0.074 g, 0.081 mmol, Strem Chemical Inc, Newburyport, Mass.), and toluene (3.3 mL) were added to a high-pressure reaction vessel. The vessel was sealed and heated at 100° C. for 24 h. After cooling to room temperature, was purified via flash chromatography on silica gel (twice, 2% MeOH in CH2Cl2 then 33% EtOAc in hexanes) to afford 2-(4-((2S)-2-methyl-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-3,3,3-trifluoro-1,2-propanediol (0.017 g) as a mixture of two isomers.

Provenance & Evidence