2-Bromo-4-methylpyridine (1) was converted to 2-bromo-4-iodomethylpyridine (3) by chlorination and iodination|3 reacted with anthrone (4) to form 10,10-bis(2-bromopyridin-4-yl-methyl)-9(10H)- anthrone (5). Methoxy group was introduced to pyridine ring by nucleophilic substitution at 3 MPa with NaOCH₃ to give 10,10-bis(2-methoxypyridin-4-yl-methyl)-9(10H)-anthrone (6). 6 was reduced by NaBH₄ to give anthracenol (7). 7 was catalyzed by p-TsOH to give pyridinylhomotriptycene (8) by an intramolecular 1,7-electrophilic dehydration.

Key words: homotriptycene, pyridinylhomotriptycene, 10,10-bis(2-methoxypyridin-4-yl-methyl)-9(10H)- anthrone, anthracenol, 1,7-electrophilic dehydration