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

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Reaction Conditions

Reaction Steps

A mixture of 4.00 g (14 mmol) of Na2CO3×10H2O, 60 ml of water and 20 ml of methanol was purged with argon for 30 min. The obtained solution was added to a mixture of 1.82 g (5.6 mmol) of 2-methyl-N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]aniline, 1.95 g (6.7 mmol) of N-[(6-Bromopyridin-2-yl)methyl]-2,6-diisopropylaniline, and 0.32 g (0.28 mmol) of Pd(PPh3)4 in 75 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 15 ml of diethyl ether. Yield 1.79 g (69%) of white crystalline powder. Anal. calc. for C32H37N3: C, 82.89; H, 8.04; N, 9.04. Found: C, 82.68; H, 7.98; N, 8.80. 1H NMR (CDCl3): δ 7.70 (m, 1H), 7.49-7.55 (m, 2H), 7.41 (d, J=8.4 Hz, 1H), 7.37-7.40 (m, 2H), 7.28 (m, 1H), 6.99-7.11 (m, 5H), 6.60 (m, 1H), 6.55 (m, 1H), 4.48 (d, J=4.6 Hz, 2H), 4.21 (s, 2H), 4.07 (br.s, 1H), 3.98 (br.s, 1H), 3.33 (sept, J=6.8 Hz, 2H), 2.04 (s, 3H), 1.19 (d, J=6.8 Hz, 12H).

Provenance & Evidence