Reaction Steps
A mixture of 2.43 g (6.00 mmol) of 2,4,6-trimethyl-N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline, 2.10 g (6.00 mmol) of N-[1-(6-bromopyridin-2-yl)-1-methylethyl]-2,6-diethylaniline, 4.33 g (15.10 mmol) of Na2CO3×10H2O, 65 ml of water, 18 ml of methanol, and 80 ml of toluene was purged with argon for 30 min. To this solution 0.35 g (0.30 mmol) of Pd(PPh3)4 was added. In argon atmosphere, this mixture was stirred for 12 h at 80° C. Then, it was cooled to room temperature, the organic layer was separated, the aqueous layer was extracted with 3×200 ml of ethyl acetate. The combined organic extract was washed with brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography on silica gel 60 (40-63 um, eluent: dichloromethane-ethyl acetate=20:1, vol.). Yield 2.66 g (82%) of yellow oil. Anal. calc. for C39H43N3: C, 84.24; H, 8.00; N, 7.76. Found: C, 84.36; H, 8.15; N, 7.61. 1H NMR (CDCl3): δ 7.87 (m, 1H. 8-H in naphtalene), 7.82 (d, J=8.4 Hz, 1H, 4-H in naphtalene), 7.78 (t, J=7.7 Hz, 1H, 4-H in pyridine), 7.70 (dd, J=7.7 Hz, J=0.6 Hz, 1H, 5-H in pyridine), 7.35-7.47 (m, 4H, 3, 5, 6, 7-H in naphtalene), 7.21 (dd, J=7.7 Hz, J=0.6 Hz, 1H, 3-H in pyridine), 6.93-7.00 (m, 3H, 3, 4, 5-H in 2, 6-Et2C6H3), 6.74 (s, 2H, 3, 5-H in mesityl), 3.96 (m, 2H, CH2N), 3.70 (br.s, 2H, NH), 2.47 (sep, J=7.6 Hz, 1H, CHMe2), 2.43 (sep, J=7.6 Hz, 1H, CHMe2), 2.21 (s, 3H, 4-Me in mesityl), 2.03 (s, 6H, 2, 6-Me in mesityl), 1.54 (s, 3H, CMeMe′), 1.47 (s, 3H, CMeMe′), 1.02 (t, J=7.6 Hz, 6H, CHMe2).
