4-Vinylpyridine → N.N-Diphenyl-7-(2-(4-pyridinyl)ethenyl)-9,9-di-n-decyl-9H-fluorene-2-amine

HRID 964840Notes

Reaction equation

HRID 964840 reaction equation
[C:1]1([N:7]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][C:14](Br)=[CH:15][CH:16]=4)[C:11]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH:70]([C:72]1[CH:77]=[CH:76][N:75]=[CH:74][CH:73]=1)=[CH2:71]>C(N(CC)CC)C>[C:1]1([N:7]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][C:14]([CH:71]=[CH:70][C:72]5[CH:77]=[CH:76][N:75]=[CH:74][CH:73]=5)=[CH:15][CH:16]=4)[C:11]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 75024-VinylpyridineHCID 80271Tri-o-tolylphosphineHCID 22723477HCID 22723477, compound

Product 1

HCID 57187974N.N-Diphenyl-7-(2-(4-pyridinyl)ethenyl)-9,9-di-n-decyl-9H-fluorene-2-amineYield 59.45%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N,N-diphenyl-7-bromo-9,9-di-n-decyl-9H-fluorene-2-amine (8.08 9,11.66 mmol), tri-o-tolylphosphine (1.42 g, 4.67 mmol), triethylamine (30 ml, degassed with nitrogen for 15 minutes), 4-vinylpyridine (2.52 ml, 23.32 mmol) and palladium(Il) acetate (0.13 g, 0.58 mmol) were added to a single-necked round bottom flask equipped with a magnetic stirrer and reflux condenser. The solution was heated at reflux by means of an oil bath under nitrogen for 16 hours. The solvent was removed under reduced pressure and the residue dissolved in methylene chloride. The organic layer was washed 3 times with water, dried over anhydrous MgSO4, filtered and concentrated. The product was purified by column chromatography using silica gel and 85:15 hexane:ethyl acetate to afford a yellow oil in 59.45% yield. The oil, upon standing for several days, gradually solidified to give a waxy solid (mp 88.4° C.-89.3° C.). Mass Spec. m/z 716 (M+), 576, (M-C10H20), 358 (M++). Elemental Analysis: Calculated for C52H64N2 : C, 87.10; H, 9.00; N, 3.90. Found: C, 87.17; H, 9.45; N, 3.35.

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe solution was heated
  4. temperatureat reflux by means of an oil bath under nitrogen for 16 hours
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe residue dissolved in methylene chloride
  7. washThe organic layer was washed 3 times with water
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe product was purified by column chromatography
  12. customethyl acetate to afford a yellow oil in 59.45% yield
  13. waitThe oil, upon standing for several days

Sources & evidence

ORD record
ord-3557b9056c684aa7a78eb4ce41aec1f6
Source dataset
uspto-grants-1998_06
Patent number
US05770737

Reaction notes

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