Toluene → 5-Phenyl-2-pyridinamine

Participants

Reaction Steps

A mixture of toluene (80 mL) and water (20 mL) was degassed with argon for 5 minutes. Sodium carbonate (9.63 g, 0.0909 mole) was added and the mixture was degassed with argon for 5 minutes. Phenylboronic acid (6.65 g, 0.05454 mole) and 2-amino-5-iodo-pyridine (10.0 g, 0.04545 mole) were then added and the mixture was degassed with argon for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (5.252 g, 0.00454 mole) was added was degassed with argon for 5 minutes. The resulting mixture was then heated to reflux for 3 hours. The mixture was diluted with ethyl acetate, and the organic layer was washed with water followed by brine solution. The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography using silica gel 60-120 mesh (1% methanol in chloroform) afforded 3.2 g (41%) of 5-phenyl-pyridin-2-ylamine. LC-MS purity: 171.08 (M+1)+, 87%.

Provenance & Evidence