Aniline → N-phenyl-3-(pyridin-2-yl)aniline

2-(3-bromophenyl)pyridine (4 g, 17.09 mmol), Pd2(dba)3 (0.156 g, 0.171 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (S-Phos) (0.281 g, 0.683 mmol), and sodium t-butoxide (2.463 g, 25.6 mmol) were mixed in 100 mL of xylene. The solution was bubbled with nitrogen for 20 min. Aniline (2.387 g, 25.6 mmol) was added. The reaction was heated up to reflux for 6 h. After cooled to rt, dichloromethane was added. The mixture was filtered through Celite®. The solvent was then evaporated. The residue was coated on Celite® and columned with 1:5 hexanes/ethyl acetate to give N-phenyl-3-(pyridin-2-yl)aniline (3.6 g, 14.62 mmol, 86% yield) as light yellow solid.

1. customThe solution was bubbled with nitrogen for 20 min
2. temperatureThe reaction was heated up
3. temperatureto reflux for 6 h
4. filtrationThe mixture was filtered through Celite®
5. customThe solvent was then evaporated

ORD-Eintrag

ord-5d01ae38b3514e6fa2bf1e2c1de2bc1f

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08871361B2