2-Bromopyridine → HCID 25027937, compound

Participants

Reaction Conditions

Reaction Steps

Under argon an oven-dried flask was charged with tris(dibenzylideneacetone)dipalladium (2.5 mg), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (4.7 mg), cesium carbonate (41.2 mg) and dioxane (0.75 mL). The mixture was stirred for 30 min, before a mixture of (S)-1-benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one (example 66, step 3) (40 mg) and 2-bromopyridine (17.1 mg) in dioxane (0.75 mL) was added. The reaction mixture was heated to 100° C. for 4 hours and was stirred at room temperature over night. The mixture was cooled to room temperature, an aqueous solution of NaHCO3 was added, the phases were separated, and the inorganic one was extracted with ethyl acetate (×3). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. Purification by chromatography (SiO2, CH2Cl2/ethyl acetate 4:1 to ethyl acetate) gave (S)-1-benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-pyridin-2-yl-imidazolidin-2-one as a light yellow solid, MS: 519.8 ([M+H]+).

Provenance & Evidence