Tris(1,1-dimethylethyl)phosphine → 2-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)-amino]-9,10-diphenylanthracene

HRID 426383Notes

Reaction equation

HRID 426383 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=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.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1>[C:28]1([N:38]([C:2]2[CH:15]=[CH:14][C:13]3[C:4](=[C:5]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:6]4[C:11]([C:12]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:3]=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

6

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 222471632-Bromo-9,10-diphenylanthraceneHCID 23676156Sodium t-butoxideHCID 59132882N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amine

Product 1

HCID 581847212-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)-amino]-9,10-diphenylanthraceneYield 42.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

3.5 g (8.6 mmol) of 2-bromo-9,10-diphenylanthracene synthesized in Step 1 of Embodiment 1, 3.2 g (9.4 mmol) of N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amine (abbreviation: PCN), 0.25 g (0.43 mmol) of bis(benzylideneacetone)palladium (0), and 2.1 g (21 mmol) of sodium tert-butoxide were put in a 200 mL three-neck flask, and the atmosphere of the flask was substituted with nitrogen. Thereafter, 50 mL of toluene and 0.86 g (0.43 mmol) of tri(tert-butyl)phosphine (10% hexane solution) were added to the mixture, and this reaction mixture was stirred for 5 hours at 80° C. After the reaction was completed, the reaction solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extracted solution was combined with the organic layer, and then dried with magnesium sulfate. After drying, this mixture was subjected to suction filtration, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (eluent:toluene). The obtained solid was recrystallized with a mixed solvent of chloroform and hexane, giving 2.6 g of 2-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)-amino]-9,10-diphenylanthracene (abbreviation: 2PCNPA) as yellow powder in 42% yield. It was confirmed by a nuclear magnetic resonance measurement (NMR) that this compound was 2-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)-amino]-9,10-diphenylanthracene (abbreviation: 2PCNPA).

Workup

  1. washthe reaction solution was washed with water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. customAfter drying
  5. filtrationthis mixture was subjected to suction filtration
  6. concentrationthe filtrate was concentrated
  7. customThe obtained residue was purified by silica gel column chromatography (eluent:toluene)
  8. customThe obtained solid was recrystallized with a mixed solvent of chloroform and hexane

Sources & evidence

ORD record
ord-5ce2e92bd91b442b9f85eb10ce568f9d
Source dataset
uspto-grants-2012_01
Patent number
US08106392B2

Reaction notes

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