反应详情

温度

23 °C

4-Bromobenzene-1,2-diamine (1.0 equivalent) and Na2CO3 (2.0 equivalents) were dissolved in DMF/H2O (5:1) at room temperature. Nitrogen was bubbled through the reaction mixture for 5 minutes and PdCl2(dppf)2 (0.1 equivalents) was added. After stirring at 23° C. for approximately 10 minutes, 2-thiopheneboronic acid (1.1 equivalents) in DMF was added and the reaction was heated at 90° C. for 12 hours. After this time, the solution was concentrated and partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting black residue was purified by silica gel chromatography (0-20% EtOAc:hexanes) to yield an orange solid. LC/MS m/z 221.1 (MH+), Rt 2.67 minutes.

1. customNitrogen was bubbled through the reaction mixture for 5 minutes
2. temperaturethe reaction was heated at 90° C. for 12 hours
3. concentrationAfter this time, the solution was concentrated
4. custompartitioned between EtOAc and H2O
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with EtOAc
7. dry with materialThe combined organic layers were dried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe resulting black residue was purified by silica gel chromatography (0-20% EtOAc:hexanes)
10. customto yield an orange solid