反应详情

温度

100 °C

A mixture of 7-benzyl-4-hydroxy-1-iodo-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (117 mg, 0.27 mmol), 5-fluoropyridine-3-boronic acid (45 mg, 0.32 mmol), Cs2CO3 (175 mg, 0.54 mmol) and Pd(PPh3)4 (31 mg, 0.027 mmol) in 5 mL of DMF was heated at 100° C. for 16 h under N2 atmosphere. After the mixture was cooled to r.t., EtOAc (50 mL) and brine (10 mL) were added. 1 M HCl was added with stirring until pH was about 4. The aqueous layer was extracted with additional EtOAc, and the combined organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (5-70% EtOAc/hexanes) to give 61 mg of the title compound. MS: (+) m/z 405.97 (M+1).

1. temperatureAfter the mixture was cooled to r.t.
2. extractionThe aqueous layer was extracted with additional EtOAc
3. dry with materialthe combined organic layer was dried over MgSO4
4. concentrationconcentrated
5. customThe crude product was purified by silica gel chromatography (5-70% EtOAc/hexanes)