N,N'-Dimethylethylenediamine → 1-[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a nitrogen-flushed tube were added 0.20 grams (0.72 mmol) (3,5-dibromo-phenyl)-pyridin-3-yl-methanone, 0.137 g (0.72 mmol) copper (I) iodide, 0.235 (0.72 mmol) cesium carbonate, 0.063 g (0.72 mmol) N,N′-dimethyl-ethane-1,2-diamine, 0.061 g (0.72 mmol) pyrrolidin-2-one and 5 mL dioxane. The tube was sealed and heated at 80° C. overnight. The reaction mixture was allowed to cool, and was filtered. The volatiles were removed under reduced pressure and the resulting material was chromatographed on silica gel with 2% methanol/chloroform to give 0.018 g of 1-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one. This material was converted to 1-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one as described in Example 75. 1H NMR (400 MHz, CD3OD): δ 9.01 (s, 1H), 8.79 (s, 1H), 8.26-8.31 (m, 2H), 8.06 (s, 1H), 7.86 (s, 1H), 7.62 (s, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.30 (d, J=3.1 Hz, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.14 (d, J=7.2 Hz, 1H), 6.67 (d, J=3.1 Hz, 1H), 4.03 (t, J=7.0 Hz, 2H), 2.63 (t, J=8.1 Hz, 2H), 2.16-2.26 (m, 2H).

Provenance & Evidence