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

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Reaction Conditions

Reaction Steps

A mixture of 2.50 g (6.7 mmol) of Na2CO3×10H2O, 69 ml of water and 22 ml of methanol was purged with argon for 30 min. The obtained solution was added to a mixture of 2.50 g (6.7 mmol) of 2-methyl-N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline, 2.70 g (6.7 mmol) of N-[(6-bromopyridin-2-yl)methyl]-2,6-bis(1-ethylpropyl)aniline, and 0.39 g (0.34 mmol) of Pd(PPh3)4 in 90 ml of toluene. This mixture was stirred for 12 h at 70° C., then cooled to room temperature. The organic layer was separated, the aqueous layer was extracted with 3×50 ml of ethyl acetate. The combined organic extract was washed with brine, dried over Na2SO4, and evaporated to dryness. The residue was re-crystallized from 5 ml of diethyl ether. Yield 2.20 g (58%) of white crystalline powder. Anal. calc. for C39H45FN3: C, 84.31; H, 8.31; N, 7.37. Found: C, 84.28; H, 8.26; N, 7.19. 1H NMR (CDCl3): δ 7.90 (d, J=8.5 Hz, 1H), 7.88 (m, 1H), 7.83 (m, 1H), 7.66 (d, J=8.5 Hz, 1H), 7.60 (m, 1H), 7.35-7.49 (m, 4H), 6.96-7.07 (m, 5H), 6.61 (m, 1H), 6.53 (m, 1H), 4.17-4.32 (m, 4H), 3.92 (br.m, 1H), 3.85 (br.s, 1H), 2.88 (m, 2H), 2.08 (s, 3H), 1.62 (m, 4H), 1.49 (m, 4H), 0.73 (t, J=7.1 Hz, 6H), 0.71 (t, J=7.1 Hz, 6H).

Provenance & Evidence