1,4-Dioxane → n-Acetyl-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carbohydrazide

Participants

Reaction Conditions

Reaction Steps

9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one (100 mg, 0.32 mmol), acetichydrazide (47 mg, 0.63 mmol), molybdenum hexacarbonyl (83 mg, 0.32 mmol), trans-di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (15 mg, 0.016 mmol), and tri-(t-butyl)phosphonium HBF4 salt (9.2 mg, 0.032 mmol) were combined in a vial, followed by dioxane (2.0 ml), DMA (1.0 ml) and N,N-diisopropylethylamine (0.22 ml, 1.3 mmol). The resulting suspension was purged with argon (subsurface bubbling) for 10 min, and then stirred at 100° C. in a sealed vial for 3 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc (3 mL), and filtered to afford N-acetyl-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carbohydrazide. 1H NMR (500 MHz, DMSO-D6) δ 11.88 (d, 1H), 10.53 (s, 1H), 10.47 (d, 1H), 9.97 (s, 1H), 8.56 (d, 1H), 8.06 (dd, 1H), 7.57 (t, 1H), 6.79 (d, 1H), 4.12 (septet, 1H), 1.94 (s, 3H), 1.38 (d, 6H). LRMS (ESI) calc'd for (C18H18N4O3) [M+H]+, 339.1; found 339.1.

Provenance & Evidence