Cesium carbonate → HCID 66743083, compound

Participants

Reaction Conditions

Reaction Steps

In a 50 mL round-bottomed flask, 5-((S)-1-methyl-pyrrolidin-2-yl)-pyridin-2-ylamine (560 mg, 3.16 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (847 mg, 3.79 mmol) and cesium carbonate (3.09 g, 9.48 mmol) were combined with dioxane (25 ml) to give a orange suspension. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (274 mg, 474 μmol, Eq: 0.15) was added followed by tris(dibenzylideneacetone)dipalladium(0) (145 mg, 158 μmol, Eq: 0.05). The reaction was degassed with argon for 10 min and heated at 95-105° C. for 4 h. No aniline starting material remained. The reaction mixture was diluted with 200 ml CH2Cl2. MgSO4 was added and the mixture was stirred for 5 min. The reaction was filtered and the filtercake was washed several times with CH2Cl2. The combined filtrate and washes were concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 1% to 2% MeOH in CH2Cl2) to afford the desired product (522 mg, 52%). (M+H)+=320 m/e.

Provenance & Evidence