Diisopropylethylamine → N1-(3-bromobenzyl)-4-(quinolin-2-ylmethoxy)benzene-1,2-diamine

Participants

Reaction Steps

To a solution of N-(3-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline (5.9 g, 13 mmol) in THF (200 mL) was added DIPEA (1.1 mL, 6.4 mmol) followed by 5% platinum on carbon (0.4 g, 1.9 mmol). The reaction vessel was evacuated and placed under 1 atmosphere of H2 atmosphere for 23 h. The mixture was then flushed with N2 and filtered through a pad of Celite. The Celite was then rinsed with additional THF and the filtrate was concentrated to dryness. The resulting residue was purified using FCC to provide 3.3 g of the title compound as a tan solid. MS (ESI): mass calcd. for C23H20BrN3O, 434.33; m/z found 435.0 [M+H]+.

Provenance & Evidence