Water → HCID 86594585, compound

Participants

Reaction Conditions

Reaction Steps

To (4S)-1-(5-bromo-2-chlorophenyl)-N-(cyanomethyl)-4-methyl-L-prolinamide (40 mg, 0.112 mmol),4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (42 mg, 0.135 mmol, prepared as described in Example 1) and catalyst PdCl2(dppf) (5 mg, 0.0034 mmol) in DMF (2 mL) under dry nitrogen was added aqueous sodium carbonate (2.0 M, 0.17 mL, 0.336 mmol). The reaction was heated to 95° C. for 1 hour and an additional aliquot of PdCl2(dppf) (365 mg, 0.45 mmol) was added and the reaction mixture was heated for 3 hours. Water was added and the product extracted with ether (3×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 4/6) to afford (4S)-1-{4′-[4-(tert-butoxycarbonyl)piperazin-1-yl]-4-chloro-1,1′-biphenyl-3-yl}-N-(cyanomethyl)-4-methyl-L-prolinamide.

Provenance & Evidence