Potassium Phosphate, Tribasic → HCID 66599487, compound

Participants

Reaction Steps

A flask containing a mixture of methyl 3-amino-6-bromo-2-(4-nitrophenyl)isonicotinate (1.70 g, 4.83 mmol), 3-(trifluoromethyl)phenylboronic acid (1.83 g, 9.66 mmol), powdered potassium phosphate tribasic (3.38 g, 15 9 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (0.460 g, 0.966 mmol), and Pd(OAc)2 (0.108 g, 0.483 mmol) was flushed with nitrogen. THF (20 mL) was added and the mixture was heated at reflux under nitrogen for 2 hr. The mixture was diluted with EtOAc and washed with water and brine. After drying with Na2SO4), the solvents removed and the residue was suspended in a mixture of 20% EtOAc in hexane. Filtration afforded methyl 3-amino-2-(4-nitrophenyl)-6-(3-(trifluoromethyl)phenyl)-isonicotinate (1.0 g, 2.2 mmol, 46% yield). MS (ESI) m/z 417.99 (M+H). 1H NMR (400 MHz, chloroform-d) δ ppm 8.39-8.47 (2H, m), 8.22-8.27 (2H, m), 8.19 (1H, d, J=7.55 Hz), 7.93-8.03 (2H, m), 7.54-7.65 (2H, m), 6.13 (2H, br. s.), 4.04 (3H, s).

Provenance & Evidence