6-Bromopyridine-2-carbaldehyde → 6-(2-{[(2-Methylphenyl)amino]methyl}-1-naphthyl)pyridine-2-carbaldehyde

Participants

Reaction Steps

A solution of 28.4 g (99.0 mmol) of Na2CO3(H2O)10 in a mixture of 150 ml of methanol and 580 ml of water was added to a mixture of 7.38 g (39.7 mmol) of 6-bromopyridine-2-carbaldehyde, 14.8 g (39.7 mmol) of 2-methyl-N-{ [1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline and 2.29 g (2.00 mmol) of Pd(PPh3)4 in 720 ml of toluene by vigorous stirring at room temperature. The resulting mixture was stirred at 80° C. for 12 h. Further on, this mixture was cooled to room temperature, the organic layer was separated, dried over MgSO4, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-ethyl acetate=100:1 and then 20:1). Yield 10.7 g (76%). Anal. calc. for C24H20N2O: C, 81.79; H, 5.72; N, 7.95. Found: C, 81.91; H, 5.80; N, 7.81. 1H NMR (CDCl3): 10.10 (s, 1H, CHO), 8.01-8.05 (m, 2H, 3,4-H in Py), 7.96 (d, J=8.6 Hz, 1H, 4-H in naphthyl), 7.90 (m, 1H, 8-H in naphthyl), 7.68-7.70 (m, 2H, 5-H in Py and 3-H in naphthyl), 7.60 (m, 1H, 7-H in naphthyl), 7.41 (m, 1H, 6-H in naphthyl), 7.81 (m, 1H, 5-H in naphthyl), 7.03 (m, 2H, 3,5-H in Ph), 6.63 (m, 1H, 4-H in Ph), 6.50 (m, 1H, 6-H in Ph), 4.22 (m, 2H, CH2N), 3.93 (br. s, 1H, NH), 2.10 (s, 3H, Me).

Provenance & Evidence