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

HRID 2047950Notes

Reaction equation

HRID 2047950 reaction equation
[CH2:1]([O:5][C:6]1[C:7]([CH3:33])=[CH:8][C:9]([CH3:32])=[C:10]([C:12]2[N:17]=[C:16]([CH:18]=[N:19][C:20]3[C:25]([CH:26]([CH3:28])[CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=3[CH:29]([CH3:31])[CH3:30])[CH:15]=[CH:14][CH:13]=2)[CH:11]=1)[CH2:2][CH:3]=[CH2:4].[C:34]1([Mg]Br)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6]1[C:7]([CH3:33])=[CH:8][C:9]([CH3:32])=[C:10]([C:12]2[N:17]=[C:16]([CH:18]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[NH:19][C:20]3[C:25]([CH:26]([CH3:28])[CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=3[CH:29]([CH3:31])[CH3:30])[CH:15]=[CH:14][CH:13]=2)[CH:11]=1)[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 59479617N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylanilineHCID 178418255HCID 178418255, compound

Product 1

HCID 59479613N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)(phenyl)methyl)-2,6-diisopropylaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In the glovebox, N-((6-(5-(but-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylaniline (1.527 g, 3.40 mmol) is dissolved in toluene (40 mL). Phenylmagnesiumbromide (3.0M in ether, 1.36 mL, 4.09 mmol) is added, and the reaction mixture stirred at room temperature for one hour, removed from the glovebox, and quenched by addition of water (60 mL), and ether (80 mL). The aqueous layer is washed with additional ether (40 mL), and the combined organic fractions are washed with brine, dried over magnesium sulfate and filtered. Solvents are removed in vacuo, and the crude product is purified by column chromatography using 10:1 hexanes:ethylacetate (Rf=0.39) to yield 1.27 g (72.0%) of a very pale yellow solid. The structure is assigned by 1H NMR as shown in FIG. 1.

Workup

  1. customremoved from the glovebox
  2. customquenched by addition of water (60 mL), and ether (80 mL)
  3. washThe aqueous layer is washed with additional ether (40 mL)
  4. washthe combined organic fractions are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customSolvents are removed in vacuo
  8. customthe crude product is purified by column chromatography
  9. customethylacetate (Rf=0.39) to yield 1.27 g (72.0%) of a very pale yellow solid

Sources & evidence

ORD record
ord-0e99a3e2840e4c44999a0647c06f8022
Source dataset
uspto-grants-2013_11
Patent number
US08592615B2

Reaction notes

Loading…