Suzuki reaction of tribromo‐2,6‐lutidine with (2‐methoxyphenyl)boronic acid gave 3,4,5‐tris(2‐methoxyphenyl)‐2,6‐lutidine in the form of a mixture of three atropisomers that were stable at room temperature. Each isomer was isolated and fully characterized, including by X‐ray structure determination. One of the isomers, being a racemic mixture, was separated into individual enantiomers by using semipreparative chiral HPLC. Their absolute stereochemistry was initially assigned on the basis of computational calculation of the CD spectra and finally confirmed by X‐ray analysis.

The electron ionization-induced fragmentation patterns of three forensically relevant Schiff bases, originating from the condensation between 2-, 3- and 4-methoxyamphetamine and the corresponding ketones, were studied. The proposed fragmentation routes and ion structures are supported by high-resolution data and B/E linked-scan and mass-analyzed ion kinetic energy spectra. The rationalization of the ortho effect, which is responsible for the formation of the [M-OCH3] fragment in the case of the imine bearing ortho-substituted methoxy group, is given.

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SummaryA series of differently substituted 3,5-diaryl-2,4,6-trimethylpyridines were prepared and characterized using the Suzuki–Miyaura coupling reaction with accordingly selected bromo-derivatives and arylboronic acids. The reaction conditions were carefully optimized allowing high yield of isolated products and also the construction of unsymmetrically substituted diarylpyridines, difficult to access by other methods.

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