Sodium Carbonate → Ethyl [7-(3-chlorophenyl)-1-oxo-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetate

Participants

Reaction Steps

To a solution of ethyl [7-(3-chlorophenyl)-6-iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetate (123 mg, 0.269 mmol) in 9 ml of 1,4-dioxane and 1 ml of water, under argon atmosphere, phenylboronic acid (130 mg, 1.07 mmol), bis(triphenylphosphine)palladium(II) dichloride (9:4 mg, 0.013 mmol), sodium carbonate (85.0 mg, 0.80 mmol) and lithium chloride (34 mg, 0.81 mmol) were successively added. The mixture was heated at 100° for 4 hour in a sealed vial. The reaction was filtered through a celite pad and the solvent evaporated to dryness. The crude was then portioned between ethyl acetate and water, the organic layer dried over sodium sulphate and the solvent removed in vacuo. Purification by flash chromatography on silica gel column (EtOAc/Hex 3/2) led to the wanted compound in 90% yield.

Provenance & Evidence