Reaction Steps
To a solution of 2.45 g (5.10 mmol) of N-[(6-{2-[(tert-butylamino) methyl]-1-naphthyl}pyridin-2-yl)methylene]-2,6-diisopropylaniline in 50 ml of hot methanol 0.53 g (8.40 mmol) of NaBH3CN was added in one portion followed by the addition of four drops of 88% formic acid. The resulting mixture was refluxed under inert atmosphere for 1 hour and then poured into 50 ml of water. The crude product was extracted with 3×20 ml of ether. The combined extract was washed by 2×50 ml of water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:5:1, vol.). Yield 1.60 g (65%) of orange oil. Anal. calc. for C33H41N3: C, 82.63; H, 8.61; N, 8.76. Found: C, 82.74; H, 8.79; N, 8.60. 1H NMR (CDCl3): 7.89 (d, J=8.3 Hz, 1H, 4-H in naphthyl), 7.86 (m, 1H, 8-H in naphthyl), 7.82 (m, 1H, 4-H in Py), 7.65 (d, J=8.3 Hz, 1H, 3-H in naphthyl), 7.47 (m, 11-1, 3-H in Py), 7.44 (m, 1H, 7-H in naphthyl), 7.33-7.40 (m, 3H, 5-H in Py and 5,6-H in naphthyl), 7.04-7.11 (m, 3H, 3,4,5-H in Ph), 4.37 (d, J=14.7 Hz, 1H, CHH′N′Bu), 4.25 (d, J=14.7 Hz, 1H, CHH′NtBu), 3.56 (m, 2H, CH2NAr), 3.33 (sept, J=7.1 Hz, 2H, CH2Me2), 2.04 (s, 1H, NHAr), 1.18 (d, J=7.1 Hz, 6H, CHMeMe'), 1.16 (d, J=7.1 Hz, 6H, CHMeMe′), 0.96 (s, 9H, tBu).
