Cesium carbonate → HCID 66743342, compound

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 3-(6-aminopyridin-3-yl)pyrrolidine-1-carboxylate (307 mg, 1.17 mmol, Eq: 1.00) and 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (313 mg, 1.4 mmol, Eq: 1.20) were combined with 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (101 mg, 175 μmol, eq: 0.15), cesium carbonate (1.14 g, 3.5 mmol, eq: 3) and tris(dibenzylideneacetone)dipalladium(0) (53.4 mg, 58.3 μmol, Eq: 0.05) in dioxane (8.0 ml). The solution was degassed with Ar. The reaction mixture heated at 100° C. for 18 h. The solution was cooled to room temperature and diluted with 100 ml DCM. The organic layer was washed with water, and then dried over MgSO4. Concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 24 g, 50% to 100% EtOAc/Hex gradient) to give (S)-tert-butyl 3-(6-(6-chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)pyridin-3-yl)pyrrolidine-1-carboxylate (456 mg, 96%). LC/MS-ESI observed [M+H]+ 405.

Provenance & Evidence