Cesium carbonate → 4-(2-Methoxy-4-nitrophenyl)-6-methylpyridazine 1-oxide

Participants

Reaction Conditions

Reaction Steps

Step L (2): A high pressure bottle was charged with 2-(2-methoxy-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.1 g, 13.8 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1:1 complex with dichloromethane, 1.0 g, 1.1 mmol), 4-bromo-6-methylpyridazine 1-oxide (2.0 g, 11 mmol, B. Buettelmann et. al US Patent Application Publication 2004/0254179 A1), cesium carbonate (in 5 mL of water, 8.0 g, 21 mmol), and 1,4-dioxane (80 mL). The mixture was degassed by bubbling nitrogen through the solution. The bottle was capped and heated at 110° C. for 2 h. The resulting mixture was filtered through diatomaceous earth (Celite®). The filtrated was concentrated in vacuo. The crude product was purified using silica gel column chromatography (EtOAc/hexane) to afford 4-(2-methoxy-4-nitrophenyl)-6-methylpyridazine 1-oxide (1.4 g, 49% yield).

Provenance & Evidence