Potassium Carbonate → 1-(1-Oxo-indan-5-yl)-3-pyridin-3-yl-imidazolidin-2-one

Participants

Reaction Steps

Using the same reaction conditions as in Example 1, 1-pyridin-3-yl-imidazolidin-2-one (I-1b: 270 mg, 1.6587 mmol) was reacted with 5-bromo-indan-1-one (350 mg, 1.6587 mmol), 1,4-dioxane (10 mL), copper iodide (31.59 mg, 0.165879 mmol), trans-1,2-diamino cyclohexane (56.976 mg, 0.4976 mmol) and potassium carbonate (458.63 mg, 3.3174 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform) afforded 300 mg of 1-(1-oxo-indan-5-yl)-3-pyridin-3-yl-imidazolidin-2-one (61.72% yield). Hydroxylamine hydrochloride (141 mg, 2.044 mmol) and sodium acetate (167.6 mg, 2.044 mmol) in 5 mL of water were added to a solution of 1-(3-oxo-indan-5-yl)-3-pyridin-3-yl-imidazolidin-2-one (200 mg, 0.6814 mmol) in ethanol (7 mL). The reaction mixture was heated to 90° C. and maintained for 6 hours. The reaction mixture was then cooled to room temperature and the solvent was distilled from the reaction mixture. The precipitate formed was collected, washed with chloroform and dried under reduced pressure to afford 200 mg of the product (90% yield).

Provenance & Evidence