N-bromobutanimide → HCID 86703241, compound

Participants

Reaction Steps

NBS (0.497 g, 2.79 mmol) was added to a mixture of 6-(4-chlorophenyl)-1-cyclopropyl-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (Step 240.2) (1.1 g, 2.79 mmol) in CCl4 (40 mL) at 0° C. The reaction mixture was stirred for 40 h at rt, concentrated, diluted with EtOAc/water, and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated. The crude product was purified by silica gel column chromatography (CH2Cl2/MeOH 95:5) to afford a white solid and mixed fractions. The mixed fractions were purified by SFC (column 2-EP 250×30 mm, 5 μm, 60 Å, Princeton; flow 100 mL/min; gradient: isocratic 5% B for 25 min; A: scCO2, B: MeOH) to afford a white solid. Both solids were dissolved in CH2Cl2 and concentrated to afford the title compound (935 mg, 70.8% yield) as a white solid. tR: 1.07 min (LC-MS 6); ESI-MS: 472.1/474.1 [M+H]+ (LC-MS 6); TLC (CH2Cl2/MeOH 95:5): Rf=0.27.

Provenance & Evidence