Potassium Hydroxide → N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylaniline

HRID 2047949Notes

Reaction equation

HRID 2047949 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]=[N:9][C:10]2[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:19]([CH3:21])[CH3:20])[CH:5]=[CH:4][CH:3]=1.[CH2:22]([O:26][C:27]1[C:28]([CH3:37])=[CH:29][C:30]([CH3:36])=[C:31](B(O)O)[CH:32]=1)[CH2:23][CH:24]=[CH2:25].[OH-].[K+]>[Br-].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[Pd+].C1COCC1>[CH2:22]([O:26][C:27]1[C:28]([CH3:37])=[CH:29][C:30]([CH3:36])=[C:31]([C:2]2[N:7]=[C:6]([CH:8]=[N:9][C:10]3[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=3[CH:19]([CH3:21])[CH3:20])[CH:5]=[CH:4][CH:3]=2)[CH:32]=1)[CH2:23][CH:24]=[CH2:25]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 594796125-(But-3-enyloxy)-2,4-dimethylphenylboronic acidHCID 59479616N-[(6-Bromo-2-pyridinyl)methylene]-2,6-bis(1-methylethyl)benzenamine

Product 1

HCID 59479617N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylaniline

Reagents, catalysts & solvents 2

HCID 178454878HCID 178454878, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In the glovebox, N-((6-bromopyridin-2-yl)methylene)-2,6-diisopropylaniline (1.392 g, 4.03 mmol) is combined with 5-(but-3-enyloxy)-2,4-dimethylphenylboronic acid (1.000 g, 4.03 mmol) and KOH (0.678 g, 12.1 mmol) and dry THF (40 mL) is added. Palladium(I) tri-tert-butylphosphine bromide, dimer [PtBu3)PdBr]2 (0.062 g, 0.040 mmol) is added and the reaction mixture is stirred for five hours, removed from the glovebox, and ether (100 mL) is added. The solution is washed with water (50 mL) and then brine (50 mL), dried over magnesium sulfate, filtered, and solvents removed by evaporation. Yield=1.86 g of orange sticky oil. The product is used without further purification.

Workup

  1. additionis added
  2. customremoved from the glovebox, and ether (100 mL)
  3. additionis added
  4. washThe solution is washed with water (50 mL)
  5. dry with materialbrine (50 mL), dried over magnesium sulfate
  6. filtrationfiltered
  7. customsolvents removed by evaporation
  8. customThe product is used without further purification

Sources & evidence

ORD record
ord-8a50c24fee944aaf8504f487d0ca5fe4
Source dataset
uspto-grants-2013_11
Patent number
US08592615B2

Reaction notes

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