Dichloromethane → Triisopropylsilyl 4-[3'-(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)[1,1'-biphenyl]-4-yl]-1-piperazinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To 2-(3-bromophenoxy)-N-(cyanomethyl)-4-methylpentanamide (1 g, 3.07 mmoles) in toluene (20 mL) was added 4-(4-{[(triisopropylsilyl)oxy]carbonyl}-1-piperazinyl)phenylboronic acid (1.25g, 3.07 mmoles) followed by solid potassium carbonate (0.85 g, 6.14 mmoles) and finally [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (250 mg, 0.31 mmoles). The reaction was stirred overnight at 80° C. and cooled to room temperature prior to taking it up in ethylacetate. The organic phase was washed three times with 1.2 N hydrochloric acid, washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography (10% EtOAc, 90% Hexanes) to give triisopropylsilyl 4-[3′-(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)[1,1′-biphenyl]-4-yl]-1-piperazinecarboxylate.

Provenance & Evidence