Triphenylphosphine → [4,4'-Bipyridin]-3-amine

Participants

Reaction Steps

4-chloro-3-nitro-pyridine (100 mg, 0.6307 mmol), 4-pyridylboronic acid (77.52 mg, 0.6307 mmol), palladium; triphenylphosphane (36.45 mg, 0.03154 mmol), K3PO4 (946.0 μL, of 2 M, 1.892 mmol) in dioxane (3 mL) was heated at 130° C. for 30 min in a microwave. The mixture was loaded on a SCX column, washed with MeOH. The product was eluted with a 2M NH3 in MeOH. The filtrate was concentrated in vacuo. The residue was dissolved in MeOH (20 mL), Pd/C 10% (42.04 mg, 0.3950 mmol) was added and the mixture was hydrogenated (H2 balloon) overnight. The catalyst was filtered off and the filtrate was concentrated in vacuo yielding [4,4′-bipyridin]-3-amine that was used in next step without further purification. MS (ES+) 172.1.

Provenance & Evidence