An Efficient C–H Arylation of a 5-Phenyl-1H-tetrazole Derivative: A Practical Synthesis of an Angiotensin II Receptor Blocker

Abstract

An efficient protocol for C–H arylation of 1-benzyl-5-phenyl-1H-tetrazole has been developed which involves an extremely small amount of commercially available [RuCl₂(p-cymene)]₂ (Ru: 0.63 mol%) and a specific amount of triphenylphosphine (ratio Ph₃P/Ru 2:1). The obtained biphenyl derivative was readily elaborated to give candesartan cilexetil, a potent angiotensin II receptor blocker by means of an efficient removal of the benzyl protecting group by palladium on carbon catalyzed transfer hydrogenation in the final step.

Key words

green chemistry - C–H activation - ruthenium - drug synthesis - protecting groups

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