Tris(1,1-dimethylethyl)phosphine → 9-{4-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]phenyl}-10-phenylanthracene

HRID 2361205Notes

Reaction equation

HRID 2361205 reaction equation
[C:1]1([C:7]2[C:8]3[C:13]([C:14]([C:21]4[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=4)=[C:15]4[C:20]=2[CH:19]=[CH:18][CH:17]=[CH:16]4)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28]1([NH:38][C:39]2[CH:40]=[CH:41][C:42]3[N:43]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[C:44]4[C:49]([C:50]=3[CH:51]=2)=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1.C(O[Na])(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[C:28]1([N:38]([C:4]2[CH:3]=[CH:2][C:1]([C:7]3[C:20]4[C:15]([C:14]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[C:13]5[C:8]=3[CH:9]=[CH:10][CH:11]=[CH:12]5)=[CH:16][CH:17]=[CH:18][CH:19]=4)=[CH:6][CH:5]=2)[C:39]2[CH:40]=[CH:41][C:42]3[N:43]([C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)[C:44]4[C:49]([C:50]=3[CH:51]=2)=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 59132882N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amineHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 588506579-{4-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]phenyl}-10-phenylanthraceneYield 43%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2.0 g (5.0 mmol) of 9-phenyl-10-(4-bromophenyl)anthracene (PA), 1.9 g (5.0 mmol) of 3-[N-(1-naphthyl)amino]-9-phenylcarbazole (PCN), 2.1 g (20 mmol) of t-butoxysodium (abbreviation: t-BuONa) were put in a 100 mL three neck flask, and nitrogen was substituted for air in the flask, and then 40 mL of toluene and 0.1 mL of tri(t-butyl)phosphine (10 wt % hexane solution) (abbreviation: P(tBu)3) were added, and the 100 mL three neck flask was depressurized and degassed. After degassing, 30 mg (0.05 mmol) of bis(dibenzylideneacetone)palladium(0) was added, and stirred for 3 hours at 80° C. After reaction, a reaction solution was washed with water and saturated saline in this order, and then an organic layer was dried with magnesium sulfate. After natural filtration, a solid which was obtained by concentrating the filtrate was purified with silica gel column chromatography (hexane:toluene=7:3). When a target substance was recrystallized with dichloromethane hexane, 1.5 g of a yellow-solid target substance was obtained in a yield of 43% (Synthesis Scheme (g-2)). This compound was measured by a nuclear magnetic resonance (NMR) method and confirmed to be was PCNPA.

Workup

  1. customdegassed
  2. customAfter degassing
  3. customAfter reaction
  4. washa reaction solution was washed with water and saturated saline in this order
  5. dry with materialan organic layer was dried with magnesium sulfate
  6. filtrationAfter natural filtration
  7. customa solid which was obtained
  8. concentrationby concentrating the filtrate
  9. customwas purified with silica gel column chromatography (hexane:toluene=7:3)
  10. customWhen a target substance was recrystallized with dichloromethane hexane

Sources & evidence

ORD record
ord-54eaa16b33f447dcace015c0b36f2f66
Source dataset
uspto-grants-2014_04
Patent number
US08686628B2

Reaction notes

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