Water → 2,6-Diisopropyl-N-[[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl](phenyl)methyl]aniline

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.30 g (2.54 mmol) of (2,6-diisopropylphenyl){[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amine in 20 ml of THF 8.60 ml (6.35 mmol) of 0.74 M PhLi in ether was added by vigorous stirring at −78° C. The reaction mixture was stirred for 10 minutes at room temperature, then 2 ml of water was added, and, finally, this mixture was poured into 50 ml of water. The product was extracted with 3×20 ml of ether. The organic extract was washed by 2×30 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: hexanes-ethyl acetate=5:1, vol.). Yield 1.30 g (86%) of yellow oil which crystallized at room temperature. Anal. calc. for C42H43N3: C, 85.53; H, 7.35; N, 7.12. Found: C, 85.72; H, 7.39; N, 6.95. For 1H NMR (in CDCl3) see FIG. 3—Top spectrum.

Provenance & Evidence