N,N'-Dimethylethylenediamine → HCID 71547397, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-bromo-2-phenylethynyl-pyridine (Example 1, step 1) (40 mg, 0.155 mmol), 4,4-dimethylpyrrolidine-2-one (21 mg, 0.186 mmol, 1.2 equiv.), potassium carbonate (64 mg, 0.465 mmol, 3 equiv.) and N,N′-dimethylethylenediamine (1.4 mg, 0.015 mmol, 0.1 equiv.) in 1 ml of dioxane was added under argon atmosphere copper(I)iodide (3 mg, 0.015 mmol, 0.1 equiv.). The mixture was stirred overnight at 100° C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and two times with ethyl acetate. The organic layers were extracted with brine, combined, dried over sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with a heptane:ethyl acetate gradient 100:0 to 30:70. The desired 4,4-dimethyl-1-(6-phenylethynyl-pyridin-3-yl)-pyrrolidin-2-one (30 mg, 67% yield) was obtained as a white solid, MS: m/e=291.1 (M+H30).

Provenance & Evidence