15889-32-4

109-04-6

30418-59-8

15889-32-4

General procedure for the synthesis of 3-(2-pyridyl)aniline from 2-bromopyridine and 3-aminophenylboronic acid: cf. Example 31; to a suspension of 2-bromopyridine (0.5 g, 3.2 mmol), 3-aminophenylboronic acid (0.49 g, 3.2 mmol), anhydrous K2CO3 (0.87 g, 6.3 mmol) and Pd(PPh3)4 (0.36 g, 0.32 mmol) in a suspension of 1,2-dimethoxyethane (50 mL) and water (0.66 mL) under argon protection. The reaction mixture was heated at 80 °C under argon atmosphere overnight. After completion of the reaction, it was cooled to room temperature and extracted by adding water and EtOAc. The organic and aqueous phases were separated, and the combined organic phase was dried with Na2SO4 and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using a mixed solvent of gradient polarity hexane-EtOAc as eluent to give 0.22 g of 3-(2-pyridinyl)aniline (Yield: 42%). LC-MS (Method 1): tR = 1.46 min; m/z = 171.2 [M + H]+.