N,N'-Dimethylethylenediamine → HCID 71252346, compound

Participants

Reaction Steps

To a mixture of (4-bromo-2-methanesulfonylphenyl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone (1.45 g) described in Preparation Example 191, pyrrolidin-2-one (0.24 mL), potassium carbonate (0.83 g) and copper(I) iodide (0.11 g) were added toluene (3 mL) and N,N′-dimethylethylenediamine (0.13 mL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with chloroform. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give 1-{4-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]-3-methanesulfonylphenyl}pyrrolidin-2-one. To a mixture of the obtained 1-{4-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]-3-methanesulfonylphenyl}pyrrolidin-2-one, palladium(II) acetate (34 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (123 mg), potassium fluoride (697 mg) and methylboronic acid (359 mg) was added tetrahydrofuran (9 mL), and the mixture was stirred with heating under reflux for 8 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (408 mg).

Provenance & Evidence