反应详情

温度

80 °C

A mixture of bis(pinacolato)diboron (0.35 g, 1.4 mmol), methyl 4-bromobenzoate (0.30 g, 1.4 mmol), palladium(II) acetate (0.01 g, 0.04 mmol), and KOAc (0.41 g, 4.2 mmol) in DMF (7.5 mL) was degassed with argon for 30 min at rt. The mixture was then heated at 80° C. for 4 h. After the mixture was cooled to rt, N-(4-bromophenyl)-6-fluoro-1,3-benzothiazol-2-amine (0.45 g, 1.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.05 g, 0.04 mmol), and saturated aqueous NaHCO3 (5 mL) were added. The mixture was heated at 85° C. overnight. Upon cooling to rt, the mixture was diluted with EtOAc. The combined organic phases were separated, dried over Na2SO4, and concentrated in vacuo. Purification by column chromatography (25% EtOAc in hexanes) yielded 0.094 g (18%) of the title compound. LC/MS m/z 379.3 (MH+); retention time 3.87 min. 1H NMR (400 MHz, CD3OD) δ 3.93 (s, 3H), 7.05 (t, 1H), 7.39-7.81 (m, 8H), 8.03 (d, 2H).

1. customwas degassed with argon for 30 min at rt
2. temperatureAfter the mixture was cooled to rt
3. temperatureThe mixture was heated at 85° C. overnight
4. temperatureUpon cooling to rt
5. customThe combined organic phases were separated
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customPurification by column chromatography (25% EtOAc in hexanes)