反应详情

温度

85 °C

6-bromoindole-3-carboxaldehyde (5 g, 22.3 mmol), potassium vinyltrifluoroborate (4.48 g, 33.5 mmol), PdCl2 (396 mg, 2.23 mmol), PPh3 (1.75 mg, 6.7 mmol) and Cs2CO3 (2.18 mg, 66.9 mmol) were combined in a 500 mL flask placed under a nitrogen atmosphere. THF (135 mL) and H2O (15 mL) were added and the yellow solution was heated at 85° C. for 2 days. The reaction was allowed to cool to RT, water was added and the mixture was extracted twice with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1) to give the title compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.4; MS (LC/MS): 172.0 [M+H]+ 170.1 [M−H]−; tR (HPLC conditions a): 2.95 min.

1. temperatureto cool to RT
2. extractionthe mixture was extracted twice with CH2Cl2
3. dry with materialThe combined organic layers were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1)