Triphenylphosphine → HCID 59508997, compound

Participants

Reaction Conditions

Reaction Steps

To the stirred mixture of 4-(6-chloro-pyrimidin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester (VIII) (0.75 g, 2 mmol) and 6-fluoro-2-methoxy-phenyl boronic acid (0.37 g, 2.2 mmol) in saturated sodium carbonate solution (4 ml) and 1,4-dioxane (4 ml) was added palladium(II) acetate (0.09 g, 0.4 mmol) followed by triphenylphosphine (0.105 g, 0.00 mmol) at room temperature under an atmosphere of nitrogen. The resulting mixture was heated to reflux at 110° C. for one hour and the reaction monitored by TLC. The reaction mixture was filtered through a celite bed and the filtrate was extracted with ethyl acetate (3×100 ml). The organic layers were separated, combined, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by preparative HPLC (C-18, AcN:H2O with 0.05% TFA) to afford 4-[6-(2-fluoro-6-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XXIII) (0.05 g, 4%).

Provenance & Evidence