Morpholine → 6-isopropyl-9-(morpholin-4-ylcarbonyl)benzo[c]-1,6-naphthyridin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one (50 mg, 0.16 mmol), molybdenum hexacarbonyl (0.042 g, 0.16 mmol), trans-di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (7.4 mg, 7.9 mmol), and tri-(t-butyl)phosphonium HBF4 salt (4.6 mg, 0.016 mmol) were added to a vial, followed by dioxane (1.0 ml), DBU (0.095 ml, 0.63 mmol) and morpholine (0.027 ml, 0.32 mmol). The resulting suspension was purged with argon (subsurface bubbling) for 5 min. The reaction mixture was stirred at 100° C. for 16 hr in a sealed vial. The reaction mixture was diluted with ACN, MeOH, and DMSO and purified directly by preparative reverse phase HPLC, eluting with an acetonitrile/water (0.05% TFA modifier) gradient to afford 6-isopropyl-9-(morpholin-4-ylcarbonyl)benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (500 MHz, DMSO D-6) δ 11.86 (d, 1H), 10.07 (d, 1H), 8.53 (d, 1H), 7.74 (dd, 1H), 7.57 (t, 1H), 6.78 (dd, 1H), 4.10 (septet, 1H), 3.70 (br s, 4H), 3.55 (br s, 2H), 3.35 (br s, 2H), 1.38 (d, 6H). LRMS (ESI) calc'd for (C20H21N3O3) [M+H]+, 352.2; found 352.1.

Provenance & Evidence