Trifluoroacetic acid → 2-chloro-1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone

Participants

Reaction Conditions

Reaction Steps

To 2-chloro-1-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone (0.60 g, 1.34 mmol) was added trifluoroacetic acid (2 mL). The reaction mixture was heated at 65° C. for 16 hours. On completion of the reaction, 1,4-dioxane (5 mL) and toluene (5 mL) were added and the solvent removed under reduced pressure to give the crude product. The crude product was then partitioned between dichloromethane (20 mL) and water (20 mL). The organic layer was separated, washed with brine (2×10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography (SiO2, gradient 60% EtOAc in hexane to 80% EtOAc in hexane) to give the pure desired product, 2-chloro-1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone as a white foamy solid (0.360 g, 83%). LCMS [M+H]: 327.

Provenance & Evidence