Scalable Synthesis of the Key Fexuprazan Intermediate and Investigation of a Reaction Mechanism.

ABSTRACT: A three-step method for the synthesis of methyl 5-(2,4-difluorophenyl)-4-methoxy-1H-pyrrole-3-carboxylate 1, a key intermediate of fexuprazan, is reported in this paper. Using low-priced sodium p-tolylsulfinate as the starting material, compound 28 was obtained with a 96.8% yield in the first step by optimizing the experimental parameters with a Box-Behnken experimental design. Subsequently, isonitrile compound 29 was obtained by dehydration. Finally, impurities 31 and 32 in the last step of the reaction were identified and converted into target product 1 by a one-pot method, which significantly improves the utilization of atoms. Key intermediate 1 was obtained via a three-step process with a yield of 68-70% and purity that exc

SUBMITTER: Wang T 

PROVIDER: S-EPMC11391555 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature