Cesium carbonate → 1-Piperazinecarboxylic acid, 4-(3-cyano-7-quinolinyl)-3-oxo-, 1,1-dimethylethyl ester

Participants

Reaction Conditions

Reaction Steps

To a 25 mL flask was added a stir bar, 7-chloroquinoline-3-carbonitrile (0.15 g, 0.79 mmol), Pd2 dba3 (0.072 g, 0.08 mmol), Xantphos (0.090 g, 0.16 mmol), cesium carbonate (0.36 g, 1.13 mmol) and tert-butyl 3-oxopiperazine-1-carboxylate (0.31 g, 1.6 mmol). The resulting mixture was degassed and purged with N2 (3×). To the flask was added 1,4 dioxane (10 mL). The resulting reaction mixture was then refluxed at 100° C. for overnight. Analysis of the reaction mixture by LC indicated that reaction had gone to completion. The solution was concentrated in vacuo and the resulting crude was dissolved in EtOAc and washed with brine, then dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was then subjected for purification by silica gel column chromatography (10% MeOH in DCM) to provide the title product.

Provenance & Evidence