Potassium Carbonate → Methyl 2-{[5-((3R)-5-Oxopyrrolidin-3-yl)-2-chlorophenyl]amino}benzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of (4R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-one (0.18 g, 0.86 mmol), methyl 2-bromobenzoate (0.37 g, 1.72 mmol), palladium acetate (0.038 g, 0.172 mmol), and Buchwald's reagent (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) (0.122 g, 0.256 mmol) was added dioxane (2 mL). The mixture was degassed by alternatively applying a vacuum and flushing with nitrogen for a few cycles. After 15 minutes, potassium carbonate (0.237 g, 1.72 mmol) was added. The mixture was stirred overnight at 100° C., and then cooled to room temperature and filtered through Celite. The filtrate was washed with an aqueous HCl solution and extracted with ethyl acetate (3 times). The ethyl acetate layers were then washed with brine and concentrated to give the title compound (13a) as a brown residue which was used directly in the next step. MS (ESI) m/z 345 (M+H)+.

Provenance & Evidence