1-Chloro-3-ethynylbenzene → (2-(3-Chloro-phenylethynyl)-4,6-dimethyl-pyridin-3-yl)amine

Participants

Reaction Steps

To a solution of Cul (5.7 mg, 30 μmol) in triethylamine (1.6 ml) were added 2-bromo-4,6-dimethyl-pyridin-3-ylamine (120 mg, 0.60 mmol, described in Example 12), (PPh3)2PdCl2 (21 mg, 30 μmol), and 1-ethynyl-3-chlorobenzene (98 mg, 0.72 mmol). The reaction mixture was stirred for 30 min. at room temperature and for 3 h under reflux. The solvent was evaporated and the crude residue was purified by flash chromatography (cyclohexane/ethyl acetate 4:1) to yield 39 mg (0.15 mmol, 25%) of (2-(3-chloro-phenylethynyl)-4,6-dimethyl-pyridin-3-yl)amine as a brown oil.

Provenance & Evidence