Dichloromethane → HCID 86732568, compound

Participants

Reaction Steps

Cesium carbonate (32.6 mg, 0.1 mmol), [3-(trifluoromethoxy)phenyl]boronic acid (20 mg, 0.1 mmol), and 1,1′-bis(diphenylphosphino)ferrocenepaladium (4 mg, 0.005 mmol) complex with dichloromethane, were subsequently added to a solution of tert-butyl 4-[2-(2,4-dimethoxybenzyl)-7-iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]piperidine-1 carboxylate (30 mg, 0.05 mmol) in 3 ml of 1,4-dioxane and 1 ml of water, under argon atmosphere. The mixture was heated at 90° for 4 hours in a sealed vial. The reaction was filtered through a celite pad and the solvent evaporated to dryness. The crude was 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 (Hex/EtOAc 8/2) afforded the compound tert-butyl 4-{2-(2,4-dimethoxybenzyl)-1-oxo-7-[3-(trifluoromethoxy)phenyl]-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl}piperidine-1-carboxylate as oil (10 mg, 32%).

Provenance & Evidence