Sodium Carbonate → (2S)-N-(Cyanomethyl)-4-methyl-2-{[(R)-[4'-(methylthio)-1,1'-biphenyl-4-yl](phenyl)methyl]oxy}pentanamide

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide (0.84 mmol, 348 mg) in toluene (5 mL) and n-propanol (1.5 mL) was added under a stream of nitrogen 4-(methylthio)phenylboronic acid (1.0 mmol, 169 mg), Pd(PPh3)4 (0.042 mmol, 48 mg), Na2CO3 (2 M, 2 mL). The mixture was degassed with a rapid stream of nitrogen bubbling through the mixture and the mixture was heated to 100° C. for 2 h. The mixture was cooled, diluted with EtOAc and washed with water. The product was isolated by chromatography (40% EtOac/Hexane).

Provenance & Evidence