2-Bromothiophene → Carbazole

HRID 2209322Notes

Reaction equation

HRID 2209322 reaction equation
C(N1[C:11]2=[CH:12][C:13]3[C:17](=[CH:18][C:10]2=C(C2SC(Br)=CC=2)C1=O)[N:16](CCCCCC)[C:15](=O)[C:14]=3[C:26]1S[C:28](Br)=[CH:29][CH:30]=1)CCCCC.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1.O.BrC1SC=CC=1>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].CO>[CH:28]1[C:15]2[NH:16][C:17]3[C:13](=[CH:12][CH:11]=[CH:10][CH:18]=3)[C:14]=2[CH:26]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 138512-BromothiopheneHCID 62657Potassium Phosphate, TribasicHCID 22272177Toluene waterHCID 866982691,5-Dihexyl-3,7-di-(5-bromothiophen-2-yl)-1H,5H-pyrrolo[2,3-f]indole-2,6-dione

Product 1

HCID 6854CarbazoleYield 460%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 1,5-dihexyl-3,7-di-(5-bromothiophen-2-yl)-1H,5H-pyrrolo[2,3-f]indole-2,6-dione (0.150 g, 0.221 mmol), 2,7-bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N-9″i-heptadecanylcarbazole (0.152 g, 0232 mmol), Pd2(dba)3 (5.0 mg), (o-tol)3P (3.0 mg), K3PO4 (0.187 g) and toluene/H2O (20 mL/1 mL) was heated at reflux for 24 h. 2-bromothiophene (0.035 g, 0.22 mmol) in toluene (1 mL) was added and the resulting mixture was stirred for another 12 h. Then, after cooling to room temperature, the mixture was dropped into methanol to precipitate. After being filtered and dried, the precipitation was Soxhlet extracted with methanol, acetone, hexane, dichloromethane. A black solid (0.170 g, 85%) was obtained.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customto precipitate
  4. filtrationAfter being filtered
  5. customdried
  6. customthe precipitation
  7. extractionextracted with methanol, acetone, hexane, dichloromethane

Sources & evidence

ORD record
ord-88b0b4de62774d648282b777662c6fe0
Source dataset
uspto-grants-2016_06
Patent number
US09379335B2

Reaction notes

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