反应详情

温度

100 °C

To a 50-mL round-bottomed flask was added 3-((2-methoxy-4-pyridinyl)methyl)-1-(2-thiophenylsulfonyl)piperazine (168 mg, 0.47 mmol), 2-(4-bromophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (184 mg, 0.57 mmol, Bioorg. Med. Chem. Lett. 2002, 12, 3009), dicyclohexyl(2′,4′,6′-triisopropyl-[1′,1′-biphenyl]-2-yl)phosphine (91 mg, 0.19 mmol, Strem, Newburyport, Mass.), tris(dibenzylideneacetone)dipalladium (43 mg, 0.05 mmol, Strem, Newburyport, Mass.), sodium tert-butoxide (137 mg, 1.43 mmol, Aldrich, St. Louis, Mo.), and toluene (5 mL). The reaction mixture was stirred at 100° C. for 18 h and allowed to cool to room temperature. The reaction mixture was diluted with saturated NH4Cl (20 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a yellow oil. The crude product was purified by silica gel chromatography, eluting with 40% EtOAc/hexanes to give 1,1,1,3,3,3-hexafluoro-2-(4-(2-((2-methoxy-4-pyridinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (121 mg) as a colorless oil.

1. temperatureto cool to room temperature
2. extractionextracted with EtOAc (2×30 mL)
3. extractionThe organic extract
4. washwas washed with saturated NaCl (5 mL)
5. dry with materialdried over Na2SO4
6. filtrationThe solution was filtered
7. concentrationconcentrated in vacuo
8. customto give the crude material as a yellow oil
9. customThe crude product was purified by silica gel chromatography
10. washeluting with 40% EtOAc/hexanes