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Solvent-Mediated Tunable Regiodivergent C6- and N1-Alkylations of 2,3-Disubstituted Indoles with p-Quinone Methides

Indium-catalyzed, solvent-enabled regioselective C6- or N1-alkylations of 2,3-disubstituted indoles with para-quinone methides are developed under mild conditions. Notably, highly selective and switchable alkylations were selectively achieved by adjusting the reaction conditions. Moreover, scalability and further transformations of the alkylation products are demonstrated, and this operationally simple methodology is amenable to the late-stage C6-functionalization of the indomethacin drug. The reaction pathways were explained with the support of experimental and density functional theory studies.

 

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A new method for regioselective alkylations of 2,3-disubstituted indoles using para-quinone methides has been developed using indium catalysts and solvents. The reaction conditions can be adjusted for highly selective and switchable alkylations, and the methodology is operationally simple and scalable. The resulting products can be further transformed and applied to the late-stage C6-functionalization of the indomethacin drug. Experimental and density functional theory studies have provided insight into the reaction pathways.

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Cat.No. Product Name Information
S1723 Indomethacin Indomethacin is a nonselective COX1 and COX2 inhibitor with IC50 of 0.1 μg/mL and 5 μg/mL, respectively, used to reduce fever, pain, stiffness, and swelling.

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