4-Bromophenol → 4-(Pyridin-2-ylamino)phenol

Participants

Reaction Steps

To a microwave reaction vessel was added 4-bromophenol (5.5773 mL, 59.317 mmol), 2-aminopyridine (5.5942 g, 59.317 mmol), Pd2(dba)3 (1.3658 g, 1.4829 mmol), 2-di-t-butylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (2.5346 g, 5.9317 mmol), and sodium tert-butoxide (10.0798 g, 118.63 mmol). The vessel was capped and flushed with argon. Toluene was added and the vessel was flushed with argon. The temperature was brought to 100° C. to stir overnight. The reaction was monitored by LCMS to completion. The solvent was evaporated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ SNAP cartridge (KP-Sil 340 g), eluting with a gradient of 1.5% to 6% methanol in DCM, to provide 4-(pyridin-2-ylamino)phenol. MS (ESI, pos. ion) m/z: 187.0 (M+1).

Provenance & Evidence