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 tetrahydrofuran (THF) (140 mL) was degassed with argon for about 1.5 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 RT and poured over EtOAc (500 mL). The organics were then washed with saturated sodium bicarbonate (NaHCO3, H2O) and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was then purified via flash chromatography (SiO2, 2:1 hexanes-dichloromethane) to afford Compound 23 (9.54 g, 98% yield) as a light yellow, crystalline solid.

Provenance & Evidence