Potassium Iodide → (2S)-N-(cyanomethyl)-4-methyl-2-{[(R)-{4-[4-(methylthio)benzoyl]phenyl}(phenyl)methyl]oxy}pentanamide

Participants

Reaction Conditions

Reaction Steps

(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide from example 68 (150 mg, 0.361 mmol), 4-(methylthio)phenyl boronic acid (67 mg, 0.398 mmol, 1.1 eg), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II)complex) (7.9 mg, 0.011 mmol, 0.03 eg), potassium iodide (180 mg, 1.08 mmol, 3 eg), potassium carbonate (149 mg, 1.08 mmol, 3 eg) were mixed together in anisole (5 mL). The reaction mixture was degased 3× with nitrogen, then heated at 90° C. under latm of CO for 18 hours. The crude reaction mixture was concentrated under high vacuum and the residue was chromatographed with 30% EtOAc/hexane to give the title compound.

Provenance & Evidence