Triethylamine → HCID 59375380, compound

Participants

Reaction Steps

To a solution of 9-bromo-6-(ethylamino)-4-iodobenzo[c]-1,6-naphthyridin-1(2H)-one (2.5 g, 5.63 mmol) in DMF at room temperature (49.3 ml) was added propiolamide (583 mg, 8.44 mmol), Copper (I) Iodide (161 mg, 0.844 mmol), triethylamine (1.569 ml, 11.26 mmol), and tetrakis(triphenylphosphine) palladium (651 mg, 0.563 mmol). The flask was put under a blanket of argon, sealed and allowed to stir overnight. The next day the reaction was diluted with 100 ml of DCM, which caused the product to precipitate out of solution. The precipitate was collected by filtration, washed with 50 ml of DCM and dried in vacuo to give the product, 3-[9-bromo-6-(ethylamino)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide. 1H NMR (600 MHz, DMSO-D6) δ 11.76 (br s, 1H), 10.00 (s, 1H), 8.40 (t, 1H), 8.27 (d, 1H), 7.79-7.76, (m, 3H), 7.47 (s, 1H), 3.66 (m, 2H), 1.25 (t, 3H). LRMS (ESI) calc'd for (C17H13BrN4O2) [M+H]+, 385.0; found 385.0.

Provenance & Evidence