Ceric ammonium nitrate → 4-(4-chlorophenyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]-pyrazol-6(1H)-one

Participants

Reaction Steps

To a stirred solution of 4-(4-chlorophenyl)-5-(4-methoxybenzyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 71.3) (2.8 g, 5.90 mmol) in CH3CN (80 mL) and H2O (20 mL) was added CAN (9.70 g, 17.69 mmol) and the reaction mixture was stirred at RT for 16 hr. The reaction mixture was quenched with brine and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 1-2.5%). The residue was triturated in CH2Cl2 to afford the title product (1.06 g, 2.93 mmol, 50% yield) as white solid. tR: 4.36 min (HPLC 1); tR: 0.98 min (LC-MS 2); ESI-MS: 355 [M+H]+ (LC-MS 2); Rf=0.39 (CH2Cl2/MeOH 9:1).

Provenance & Evidence