Potassium Phosphate, Tribasic → Methyl 3-amino-2-(4-(benzyloxy)phenyl)-6-(4-methoxyphenyl)isonicotinate

Beteiligte Stoffe

Reaktionsschritte

A flask containing dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (132 mg, 0.322 mmol), methyl 3-amino-2-(4-(benzyloxy)phenyl)-6-bromoisonicotinate (665 mg, 1.61 mmol), 4-methoxyphenylboronic acid (293 mg, 1.93 mmol), palladium(II) acetate (36.1 mg, 0.161 mmol), and potassium phosphate tribasic (1025 mg, 4.83 mmol) was flushed with nitrogen. Tetrahydrofuran (16 mL) was added and the reaction was heated at reflux overnight. The reaction was partitioned between EtOAc and water. The organic phase was separated, washed with brine, dried with sodium sulfate and the solvent removed. Radial silica gel chromatography (step gradient elution with hexane containing 0 to 10% EtOAc) afforded 556 mg of methyl 3-amino-2-(4-(benzyloxy)phenyl)-6-(4-methoxyphenyl)-isonicotinate as a yellow oil. MS (ESI) m/z 441.2 (M+H). 1H NMR (CDCl3) δ ppm 8.01 (1H, s), 7.92 (2H, d, J=8.85 Hz), 7.67 (2H, d, J=8.85 Hz), 7.44-7.48 (2H, m), 7.40 (2H, t, J=7.63 Hz), 7.35 (1H, d, J=7.32 Hz), 7.10 (2H, d, J=8.85 Hz), 6.94 (2H, d, J=8.85 Hz), 5.94 (2H, br. s.), 5.13 (2H, s), 3.95 (3H, s), 3.83 (3H, s).

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