反应详情

To a microwave vial containing (E)-methyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (100 mg, 0.294 mmol) in DMA (2.5 mL) was added (R)-1-(2-bromophenyl)ethanol (118 mg, 0.588 mmol), chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-i-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II) (BrettPhos Palladacycle 1st generation, 23.47 mg, 0.029 mmol), trimethylacetic acid (90 mg, 0.881 mmol) and potassium carbonate (122 mg, 0.881 mmol) The microwave vial was sealed, purged and back-filled with nitrogen. The reaction mixture subjected to microwave irradiation for 2 h at 150° C. Upon completion the reaction was diluted with EtOAc, and washed with water and brine. The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resulting crude material was purified by column chromatography (SiO2, 0-30% EtOAc/heptane) to afford (R,E)-methyl 3-(4-((2-(2-(1-hydroxyethyl)phenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (27.5 ms, 0.060 mmol, 20% yield). LC/MS (m/z, MH+): 459.0.

1. customwas sealed
2. custompurged
3. additionback-filled with nitrogen
4. customirradiation for 2 h at 150° C
5. additionUpon completion the reaction was diluted with EtOAc
6. washwashed with water and brine
7. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe resulting crude material was purified by column chromatography (SiO2, 0-30% EtOAc/heptane)