2,2'-Bipyridine → 4-(4-chlorophenyl)-1-cyclopropyl-5-(4-methoxybenzyl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence