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

HRID 634054Notes

Reaction equation

HRID 634054 reaction equation
[Br:1][C:2]1[N:7]=[C:6](/[C:8](=[N:10]/[C:11]2[C:16]([CH:17]([CH3:19])[CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=2[CH:20]([CH3:22])[CH3:21])/[CH3:9])[CH:5]=[CH:4][CH:3]=1.[CH3:23][Al](C)C.[OH-].[K+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[C:16]([CH:17]([CH3:18])[CH3:19])=[CH:15][CH:14]=[CH:13][C:12]=2[CH:20]([CH3:22])[CH3:21])([CH3:23])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 16682925TrimethylaluminumHCID 178463283HCID 178463283, compound

Product 1

HCID 117652744N-[1-(6-Bromopyridin-2-yl)-1-methylethyl]-2,6-diisopropylaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

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).

Workup

  1. additionwas added dropwise
  2. stirringstirred for 25 min at 40° C.
  3. temperaturecooled to 0° C.
  4. customThe aqueous layer was separated
  5. washthe organic layer was washed with 80 ml of water, 80 ml of brine
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-fc1f98f56bb04685acb6a9c4014b190f
Source dataset
uspto-grants-2016_04
Patent number
US09321858B2

Reaction notes

Loading…