Potassium Carbonate → 1-(4-Cyano-benzyl)-6-methyl-4-oxo-5-phenyl-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

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Reaction Conditions

Reaction Steps

To a solution of 5-bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide (preparation 8, 80 mg, 0.156 mmol), phenylboronic acid (27 mg, 0.22 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (11 mg, 0.016 mmol) in acetonitrile (2 mL) is added 2 M aqueous K2CO3 solution (0.16 mL, 0.32 mmol). After stirring for 72 h at 75° C., the reaction mixture is filtered, basified with aqueous NH4OH solution and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 59 mg (74% of theory); ESI mass spectrum: [M+H]+=512; Retention time HPLC: 0.98 min (Z003—001).

Provenance & Evidence