Synthesis of Felbinac acid and Felbinac ester via PEPPSI palladium N-heterocyclic carbene catalytic system
Year: 2025
Type: article
Abstract: Ethyl-4-biphenylacetate (Felbinac ester) and 4-biphenylacetic acid (Felbinac acid) are common active metabolites of non-steroidal anti-inflammatory drugs (NSAIDs) and are frequently used in the treatment of muscle inflammation and arthritis. The current studies synthesized Felbinacs via a Suzuki-Miyaura cross-coupling reaction mediated through PEPPSI-palladium N-heterocyclic carbene as a catalyst. The catalyst was synthesized through N-benzylation of benzimidazole followed by N-butylation of the resulting N-benzylbenzimidazole to yield the N-benzyl-N-butylbenzimidazolium bromide (the pre-carbene). The pre-carbene was then reacted with palladium bromide (PdBr2) in 3-methylpyridine, to produce the pre-catalyst (Pd-NHC-Py-Br2). The intermediates and the pre-catalyst were characterized using 1H and 13C NMR, FT-IR, and elemental analyses. The pre-catalyst was used to mediate the synthesis of 4-biphenylacetic acid (Felbinac acid) and 4-biphenylacetate (Felbinac ester) from the coupling reaction of Ethyl-4-bromophenyl acetate with phenylboronic acid. The Pd-NHC-Py-Br2 pre-catalyst demonstrated excellent air and moisture stability.
Source: Figshare
Authors: Suleiman, Umar B., Ibrahim, Mansur B., Muhammad, Aminu, Zarewa, Sani. A.
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W6902385144
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