Toluene → HCID 86670311, compound

Participants

Reaction Conditions

Reaction Steps

A 20 mL vial was charged with (R)-2-methylpiperazine (0.357 g, 3.56 mmol, Sigma-Aldrich, St. Louis, Mo.), 2-(4-bromophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.00 g, 3.10 mmol, Bioorg. Med. Chem. Lett. 2002, 12, 3009), sodium tert-butoxide (0.625 g, 6.50 mmol) and 6 mL of toluene. To this was added dicyclohexyl(2′,6′-diisopropoxybiphenyl-2-yl)phosphine (RuPhos) (0.022 g, 0.046 mmol, Strem Chemical Inc, Newburyport, Mass.), tris(dibenzylideneacetone)dipalladium (0) (0.014 g, 0.015 mmol, Strem Chemical Inc, Newburyport, Mass.). The vial was sealed in heated at 100° C. for 12 h. After that time, the mixture was diluted with water (20 mL) and extracted with EtOAc (2×50 mL). The combined extracts were dried (MgSO4) and concentrated to give 1,1,1,3,3,3-hexafluoro-2-(4-((3R)-3-methyl-1-piperazinyl)phenyl)-2-propanol (0.950 g) as an oil which was used without purification.

Provenance & Evidence