反应详情

温度

90 °C

To a solution of 2-benzyl-5-chloro-4-methoxypyridazin-3(2H)-one (20 g, 80 mmol) and 4-chlorophenylboronic acid (15.6 g, 100 mmol) in toluene/EtOH (2:1, 600 mL) at RT under argon was added (Ph3P)4Pd (1.85 g, 1.8 mmol) and 2 M aqueous Na2CO3 solution (160 mL, 320 mmol). The resulting suspension was heated at 90° C. for 16 h with stirring. HPLC/MS indicated about 4% of the 2-benzyl-5-chloro-4-methoxypyridazin-3(2H)-one still remained. After cooling the reaction mixture to RT, the solution was extracted with CH2Cl2 (2×150 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum. The crude product was purified by silica gel column chromatography (ISCO) eluting with hexanes/EtOAc to obtain pure title compound, 2-Benzyl-5-(4-chlorophenyl)-4-methoxypyridazin-3(2H)-one, (21.7 g, 83%) as a white solid. MS [M+H]+ 327; HPLC retention time=3.85 min.

1. temperatureAfter cooling the reaction mixture to RT
2. extractionthe solution was extracted with CH2Cl2 (2×150 mL)
3. dry with materialThe combined organic layers were dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated under vacuum
6. customThe crude product was purified by silica gel column chromatography (ISCO)
7. washeluting with hexanes/EtOAc