Potassium Hydroxide → N-[1-(6-Bromopyridin-2-yl)-1-methylethyl]-2,6-diisopropylaniline

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Reaction Steps

In argon atmosphere, to a solution of 3.61 g (10.0 mmol) of N-[(1E)-1-(6-bromopyridin-2-yl)ethylidene]-2,6-diisopropylaniline in 80 ml of dry toluene cooled to 0° C. a solution of 1.44 g (20.0 mmol) of AlMe3 in 20 ml of dry toluene was added dropwise by vigorous stirring for ten minutes. The resulting mixture was slowly warmed to room temperature, stirred for 25 min at 40° C., cooled to 0° C., and then 80 ml of 5% KOH was added dropwise for 1 h at this temperature. The aqueous layer was separated, the organic layer was washed with 80 ml of water, 80 ml of brine, dried over Na2SO4, and then evaporated to dryness. Yield 3.52 g (94%) of yellowish crystalline solid. Anal. calc. for C20H27BrN2: C, 64.00; H, 7.25, N, 7.46. Found: C, 64.11; H, 7.19; N, 7.40. 1H NMR (CDCl3): δ 7.48-7.54 (m, 2H, 4, 5-H in pyridine), 7.34 (dd, J=6.9 Hz, J=1.6 Hz, 1H, 3-H in pyridine), 7.04-7.08 (m, 3H, 3, 4, 5-H in 2, 6-iPr2C6H3), 3.98 (br.s, 1H, NH), 3.15 (sep, J=6.9 Hz, 2H, CHMe2), 1.44 (s, 6H, Me2C), 7.08 (d, J=6.9 Hz, 12H, CHMe2).

Provenance & Evidence