3-Aminophenylboronic acid → 3-(1-trityl-1H-imidazol-4-yl)aniline

Participants

Reaction Conditions

Reaction Steps

(3-Aminophenyl)boronic acid (1.0 g, 7.3 mmol), 4-bromo-1-trityl-1H-imidazole (2.8 g, 7.3 mmol), tri-t-butylphosphonium tetrafluoroborate (424 mg, 1.5 mmol) and KF (1.4 g, 24.1 mmol) are added into dry THF (20 mL) and argon is bubbled through the mixture for 10 min. Tris-(dibenzylideneacetone)dipalladium(0) (669 mg, 0.7 mmol) is added and the reaction mixture is sealed and heated at 60° C. for 16 hrs. The solid is filtered and the filtrate is diluted with EtOAc (250 mL). The solution is washed with H2O (3×100 mL), brine (100 mL), dried (Na2SO4) and concentrated. The crude product is purified by flash column chromatography using methanol/CH2Cl2 to afford the title compound (1.1 g, 36%).

Provenance & Evidence