Water → 6-Isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one (200 mg, 0.631 mmol), molybdenum hexacarbonyl (166 mg, 0.631 mmol), trans-di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (29.6 mg, 0.0320 mmol), and tri-(t-butyl)phosphonium HBF4 salt (18.3 mg, 0.0630 mmol) were added to a vial, followed by dioxane (2 ml), DBU (0.38 ml, 2.52 mmol) and water (0.114 mL, 6.31 mmol). The resulting suspension was purged with argon (subsurface bubbling) for 5 min, the heated at 100° C. for 18 hr. The reaction mixture was cooled to room temperature, diluted with water (25 mL), and LiOH (45.3 mg) was added. The aqueous layer was washed with ethyl acetate (25 mL). The aqueous layer was acidified with 1 M citric acid (2.5 mL), and the resulting solid was collected by vacuum filtration, then dried under high vacuum at 50° C. for 2 hours to afford 6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxylic acid. LRMS (ESI) calc'd for (C16H14N2O3) [M+H]+, 283.1; found 283.0.

Provenance & Evidence