Cesium carbonate → HCID 46222817, compound

Participants

Reaction Conditions

Reaction Steps

A 100-mL pressure flask is equipped with a magnetic stirrer was charged with tert-butyl-N-(piperidin-3-yl)benzamide (130 mg, 0.5 mmol), dioxane (10 mL), 6-chloro-4(1,5-dimethyl-1H-pyrazol-3-ylamino)-2-methylpyridazin-3(2H)-one (127 mg, 0.5 mmol), and cesium carbonate (326 mg, 1 mmol). Argon is bubbled through the solution whilst sonicating for 15 min. Tris(dibenzylideneacetone)dipalladium (0) (46 mg, 0.05 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (66 mg, 0.1 mmol) were then added, the flask was sealed and heated to 120° C. for 8 h. The resulting mixture was diluted with dichloromethane (300 mL) and washed with water (120 mL) filtered through a pad of celite, concentrated and purified by flash chromatography on silica gel to afford a 65% yield of (R)-4-tert-butyl-N-(1-(5-(1,5-dimethyl-1H-pyrazol-3-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)piperidin-3-yl)benzamide as a white solid (155 mg, 0.325 mmol).

Provenance & Evidence