Reaction Steps
A mixture of 2.17 g (6.00 mmol) of N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}-aniline, 4.33 g (6.00 mmol) of N-[1-(6-bromopyridin-2-yl)-1-methylethyl]-2,6-diethylaniline and 1.60 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. This mixture was stirred for 12 h at 80° C., then 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 2.35 g (76%) of yellow oil. Anal. calc. for C35H37N3: C, 84.13; H, 7.46; N, 8.41. Found: C, 84.34; H, 7.55; N, 8.35. 1H NMR (CDCl3): δ 7.87-7.90 (m, 2H, 4, 8-H in naphtalene), 7.81 (t, J=7.8 Hz, 1H, 4-H in pyridine), 7.70 (dd, J=7.8 Hz, J=0.6 Hz, 1H, 5-H in pyridine), 7.67 (d, J=8.6 Hz, 1H, 3-H in naphtalene), 7.45-7.49 (m, 2H, 5, 7-H in naphtalene), 7.38-7.42 (m, 1H, 6-H in naphtalene), 7.31 (dd, J=7.8 Hz, J=0.6 Hz, 1H, 3-H in pyridine), 7.10 (m, 2H, 3, 5-H in Ph), 6.93-7.00 (m, 3H, 3, 4, 5-H in 2, 6-Et2C6H3), 6.66 (m, 1H, 4-H in Ph), 6.58 (m, 2H, 2, 6-H in Ph), 4.12-4.28 (m, 4H, CH2NH and NHCMe2), 2.44 (q, J=7.6 Hz, 4H, CH2Me), 2.43 (q, J=7.6 Hz, 4H, CH2Me), 1.54 (s, 3H, CMeMe′), 1.44 (s, 3H, CMeMe′), 1.02 (t, J=7.6 Hz, 6H, CH2Me).
