Aniline → 2,6-dichloro-N-phenylpyridin-3-amine

Reaction equation

Clc1ccc(I)c(Cl)n1.Nc1ccccc1>CC(=O)O.CC(=O)O.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>Clc1ccc(Nc2ccccc2)c(Cl)n1

Participants

Conditions

Temperature: 120 °C

Procedure

The reaction vessel was charged with nitrogen, BINAP (2.491 mg, 4.00 µmol) and diacetoxypalladium (0.898 mg, 4.00 µmol) were dilutet in toluene (2 ml) and flushed with nitrogen.2,6-dichloro-3-iodopyridine (0.027 g, 0.1 mmol), aniline (10.96 µl, 0.12 mmol) and cesium carbonate (0.163 g, 0.50 mmol) were weight in another flask and flushed with nitrogen. The Pd-BINAP mixture was subjoined and the reaction mixture was warmed to 120° C and stirred over night. The reaction was monitored using LC/MS. No product could be obtained.