Cesium carbonate → HCID 58540266, compound

Participants

Reaction Conditions

Reaction Steps

A 25-mL three-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet was charged with 6c (170 mg, 0.98 mmol), 4-bromo-6-chloropyridazin-3(2H)-one (411 mg, 1.97 mmol), cesium carbonate (956 mg, 8.61 mmol), and 1,4-dioxane (7 mL). After bubbling nitrogen through the resulting suspension for 30 min, Xantphos (48 mg, 0.08 mmol) and tris(dibenzylideneacetone)dipalladium(0) (45 mg, 0.05 mmol) were added, and the reaction mixture was heated for 16 h in a 130° C. bath. After this time, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica to afford a 41% yield (121 mg) of 6e as an off-white solid: mp 263-265° C.; 1H NMR (300 MHz, DMSO-d6) δ 13.29 (s, 1H), 1.0.10 (s, 1H), 8.75 (dd, 2H, J=4.8, 1.8 Hz), 8.52 (s, 1H), 8.35 (d, 1H, J=9.3 Hz), 8.11 (dd, 2H, J=4.5, 1.5 Hz), 8.01 (d, 1H, J=9.3 Hz); MS (ESI+) 301.1 (M+H).

Provenance & Evidence