P-Anisidine → 5-Bromo-N-(4-methoxyphenyl)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dibromopyridine (1.5 g, 6.3 mmol), p-anisidine (0.94 g, 7.60 mmol), (R)-(+)-2,2′-bis(diphenyl-phosphino)-1,1′-binapthyl (0.16 g, 0.25 mmol) and sodium tert-butoxide (0.85 g, 8.86 mmol) in toluene (15 ml) is deoxygenated using argon before adding Pd2(dba)3 (0.116 g, 0.13 mmol) and heating the mixture at 70° C. for 16 hours. The mixture is diluted with diethyl ether, washed with brine, dried over Na2SO4 and concentrated. The residue is chromatographed on silicagel to afford the product; 1H NMR (400 MHz, CDCl3): δ 8.16 (d, J=2.42 Hz, 1H), 8.04 (d, J=1.82 Hz, 1H), 7.30 (m, 1H), 7.09 (m, 2H), 6.90 (m, 2H), 5.89 (s, 1H), 3.81 (s, 3H).

Provenance & Evidence