Tris(1,1-dimethylethyl)phosphine → Carbazole

HRID 2281179Notes

Reaction equation

HRID 2281179 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[N:19]3[C:20]4[C:7](=[CH:8][CH:9]=[CH:10][C:11]=4C4C(C3=O)=CC=CC=4)[C:6]=2[CH:22]=1.CC([O-])(C)C.[Na+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>C1(C)C=CC=CC=1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:4]1[C:5]2[NH:19][C:20]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:22]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 67466017HCID 67466017, compound

Product 1

HCID 6854Carbazole

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

6.5 g (23 mmol) of 5-amino-7b-azabenzo[e]acephenanthrylen-8-one, 7.1 g (23 mmol) of 2,2′-dibromodiphenyl, 16 g (72 mmol) of NaOtBu, 1.4 g (1.58 mmol) of Pd2 dba3 and 6.3 ml (6.3 mmol) of t-Bu3P are heated at 110° C. for 36 h in 150 ml of toluene under a protective-gas atmosphere. After cooling, the precipitated solid is filtered off with suction, washed with water and ethanol and dried. The residue is extracted with hot toluene, recrystallised from toluene and finally sublimed in a high vacuum. The yield after sublimation is 7 g (16 mmol, 71%) with a purity of 99.9%.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid is filtered off with suction
  3. washwashed with water and ethanol
  4. customdried
  5. extractionThe residue is extracted with hot toluene
  6. customrecrystallised from toluene
  7. customThe yield after sublimation

Sources & evidence

ORD record
ord-3ec813d4ec134e1bb46e6030e3644574
Source dataset
uspto-grants-2015_09
Patent number
US09139582B2

Reaction notes

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