反应详情

温度

80 °C

A screw cap vial was charged with (E)-ethyl 3-(2-amino-5-bromophenyl)acrylate (0.820 g, 2.086 mmol), xantphos (0.092 g, 0.159 mmol), tris(dibenzylideneacetone)dipalladium (0.073 g, 0.080 mmol), 1,4-Dioxane (3.18 ml), and DIPEA (1.108 ml, 6.37 mmol). The vial was purged with Argon, sealed and heated to 80° C. for 10 minutes. The reaction was cooled to RT and benzyl mercaptan (0.395 ml, 3.34 mmol) was added and the reaction was continued heating at 80° C. for an additional 30 minutes. The reaction was cooled to RT, diluted with water and extracted with DCM (3×). The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The resulting material was concentrated, dissolved in minimal DCM and purified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 0.80 g of (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate. m/z (ESI) 314.1 (M+H)+.

1. customA screw cap vial
2. customThe vial was purged with Argon
3. customsealed
4. temperatureThe reaction was cooled to RT
5. temperaturethe reaction was continued heating at 80° C. for an additional 30 minutes
6. temperatureThe reaction was cooled to RT
7. extractionextracted with DCM (3×)
8. washThe combined organics were washed with water and brine
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. concentrationThe resulting material was concentrated
13. dissolutiondissolved in minimal DCM
14. custompurified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane)