2-Bromopyridine → 3-(2-Pyridyl)aniline

Participants

Reaction Steps

3-Aminophenylboronic acid hemisulphate (5.58 g, 30 mmol), 2-bromopyridine (2.7 ml, 28 mmol), Pd(PPh3)2Cl2 (100 mg, 0.5 mol %), 2M K2CO3 (50 ml) were refluxed in 1,2-dimethoxyethane (50 ml) for 24 h under N2. The mixture was diluted with CH2Cl2 (100 ml) and washed with sat. NaHCO3 (50 ml). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure. Flash-chromatography with CH2Cl2 as eluent gave 3-(2-pyridyl)aniline as a yellow oil, 1.0 g (21%). 3-(2-Pyridyl)aniline was transformed by Method B and Method G (using cyclohexanecarboxaldehyde). M.p. 213–216° C.

Provenance & Evidence