Trimethyltin chloride → HCID 86007195, compound

Participants

Reaction Steps

Suzuki coupling of commercially available 3-bromoaniline, 25, and 3,5-dimethylboronic acid afforded 3-(3,5-dimethylphenyl)aniline, 26, in high yields. Treatment of 26 with 2-chlorobenzoic acid, 27, gave N-3-(3,5-dimethylphenyl)anthranilic acid, 28, which was converted to 9-bromo-3-(3,5-dimethylphenyl)acridine, 29, using phosphorous oxybromide. As expected, we observed that 9-bromo-1-(3,5-dimethylphenyl)acridine was formed as a major by-product during ring construction. Lithiation of 29 at −78° C. followed by stannylation with trimethylstannyl chloride resulted in the formation of 3-(3,5-dimethylphenyl)-9-trimethylstannylacridine, 30, in high yields. Employing stannane 30 and 1,8-dibromonaphthalene, 31, in a CuO-promoted Stille coupling previously developed in our laboratories yielded 1,8-bis(3,3′-(3,5-dimethylphenyl)-9,9′-diacridyl)naphthalene, 32. Oxidation of 32 using m-chloroperoxybenzoic acid gave 1,8-bis(3,3′-(3,5-dimethylphenyl)-9,9′-diacridyl)naphthalene N,N′-dioxide, 33.

Provenance & Evidence