Propynamide → 3-(9-Bromo-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl)prop-2-ynamide

Participants

Reaction Steps

9-bromo-4-iodo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one (140 mg, 0.32 mmol), propynoic acid amide (26 mg, 0.38 mmol), copper (I) iodide (9.0 mg, 0.047 mmol), and Pd(Ph3P)4 (37 mg, 0.032 mmol) were added to a vial, followed by DMF (1.5 ml) and TEA (0.13 ml, 0.95 mmol). The resulting suspension was purged with argon (subsurface bubbling) for 10 min, and then stirred for 15 hr at room temperature. The reaction mixture was diluted with DMF and purified directly by reverse phase preparative HPLC using an acetonitrile/water (with 0.05% TFA as a modifier) gradient to afford 3-(9-bromo-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl)prop-2-ynamide. 1H NMR (500 MHz, DMSO-D6) δ 12.33 (br s, 1H), 10.21 (d, 1H), 8.46 (d, 1H), 8.04 (s, 1H), 7.93 (dd, 1H), 7.91 (br s, 1H), 7.58 (s, 1H), 4.07 (septet, 1H), 1.40 (d, 61-1). LRMS (ESI) calc'd for (C18H14BrN3O2) [M+H]+, 384.0; found 384.0.

Provenance & Evidence