反应详情

温度

120 °C

To a mixture of 2-(3-bromo-phenyl)-6-fluoro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (1.0 g, 2.6 mmol), palladium acetate (17.5 mg, 0.078 mmol), cesium carbonate (1.7 g, 5.2 mmol), xantphos (60.2 mg, 0.10 mmol) and 1-(ortho-tolyl)piperazine hydrochloride (830 mg, 3.9 mmol) in toluene (30 mL) was stirred at 120° C. for 12 hours. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×100 mL), washed with saturated aqueous sodium chloride (2×50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company)(20% ethyl acetate/hexanes) to afford 6-fluoro-3,3-dimethyl-2-[3-(4-o-tolyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (0.80 g, 63%) as a white solid: LC/MS m/e calcd for C30H34FN3O2 (M+H)+: 488.6, observed: 488.3.

1. concentrationThen the reaction mixture was concentrated in vacuo
2. extractionthe residue was extracted with ethyl acetate (2×100 mL)
3. washwashed with saturated aqueous sodium chloride (2×50 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated in vacuo
6. customPurification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company)(20% ethyl acetate/hexanes)