Water → 4-(5-bromopyridin-2-yl)-N,N-diphenylaniline

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(diphenylamino)phenylboronic acid (7.00 g, 24.2 mmol), 5-bromo-2-iodopyridine (7.56 g, 26.6 mmol), tetrakis(triphenylphosphine)palladium(0) (1.40 g, 1.21 mmol), Na2CO3 (9.18 g, 86.6 mmol), H2O (84 mL) and THF (140 mL) was degassed with argon for about 1.5 hours (h) while stirring. The stirring reaction mixture was then maintained under argon at 80° C. for about 19 h. Upon confirming consumption of the starting material by thin layer chromatography (TLC) (SiO2, 19:1 hexanes-EtOAc), the reaction was cooled to room temperature (RT) and poured over EtOAc (500 mL). The organics were then washed with sat. NaHCO3, H2O and brine, dried over MgSO4, filter and concentrated in vacuo. The crude product was then purified via flash chromatography (SiO2, 2:1 hexanes-dichloromethane) to afford compound 1 (9.54 g, 98% yield) as a light yellow, crystalline solid.

Provenance & Evidence