反应详情

温度

70 °C

To a stirred solution of 4-(4-chlorophenyl)-5-(4-methoxybenzyl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 85.4) (8.76 g, 23.82 mmol) in 1,2-dichloroethane (100 mL) were added cyclopropylboronic acid (4.09 g, 47.6 mmol), copper (II) acetate (5.19 g, 28.6 mmol), Na2CO3 (5.05 g, 47.6 mmol) and 2,2′-bipyridine (3.72 g, 23.82 mmol) and the resulting mixture was stirred 16 h at 70° C. The reaction mixture was quenched with a saturated aq. NaHCO3 solution and extracted with EtOAc. The combined organic layers were washed with saturated aq. NaHCO3 solution, dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (hexane/EtOAc 15-30%) to afford the title product (3.27 g, 7.62 mmol, 32% yield) as yellow solid. tR: 5.77 min (HPLC 1); tR: 1.27 min (LC-MS 2); ESI-MS: 408 [M+H]+ (LC-MS 2); Rf=0.65 (hexane/EtOAc 1:1).

1. customThe reaction mixture was quenched with a saturated aq. NaHCO3 solution
2. extractionextracted with EtOAc
3. washThe combined organic layers were washed with saturated aq. NaHCO3 solution
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 15-30%)