Potassium Phosphate, Tribasic → 4'-Amino-5'-methoxy-N,2'-dimethylbiphenyl-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

The mixture of 4-chloro-2-methoxy-5-methylaniline (2.0 g, 11.7 mmol), 4-(methylcarbamoyl)phenylboronic acid (2.08 g, 11.7 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.20 g, 2.9 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), and K3PO4 (7.4 g, 34.9 mmol) in 80 mL of n-butanol is degassed and heated at 130° C. overnight. The reaction mixture is filtered through a pad of celite, and concentrated in vacuo. The crude product mixture is partitioned between EtOAc and brine, the collected organic extracts are dried (Na2SO4), concentrated, and purified by silica gel chromatography (EtOAc/Hexanes:1/4) to afford 4′-Amino-5′-methoxy-N,2′-dimethylbiphenyl-4-carboxamide; ESMS m/z 271.1 (M+H+).

Provenance & Evidence