Ethanol → 7H-Dibenzo(a,g)carbazole

HRID 530767Notes

Reaction equation

HRID 530767 reaction equation
C([N:4]1[C:16]2[C:11](=[CH:12][C:13](Br)=[C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]3=2)[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]1[CH:25]=[CH:24][CH:23]=[CH:22][C:9]1=2)(=O)C.S1C2C=CC=CC=2N=C1C1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:22]1[C:9]2=[C:10]3[C:5](=[CH:6][CH:7]=[C:8]2[CH:25]=[CH:24][CH:23]=1)[NH:4][C:16]1[C:11]3=[CH:12][CH:13]=[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]2=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 57655345HCID 57655345, compoundHCID 712778947-acetyl-12-bromo-7H-dibenzo [a,g]carbazole

Product 1

HCID 91607H-Dibenzo(a,g)carbazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Following the above procedure, Suzuki coupling of 3.8 g of 7-acetyl-12-bromo-7H-dibenzo [a,g]carbazole and 2.7 g of (4-benzo[d]thiazol-2-yl) phenylboronic acid were stirred together in 30 ml of toluene. To this was added 0.02 g of tetrakis(triphenylphosphine)palladium, 2.1 g of potassium carbonate and 10 ml of aqueous ethanol were added and refluxed under nitrogen for 6 h. The reaction was quenched with water and the toluene layer was removed and passed through a celite column. The organic layers were combined and then evaporated in a rotary evaporator under vacuum to yield 4.1 g of 7-acetyl-12-[4-benzo[d]thiazol-2-yl) phenyl]-7H-dibenzo[a,g]carbazole as a white solid.

Workup

  1. additionwere added
  2. temperaturerefluxed under nitrogen for 6 h
  3. customThe reaction was quenched with water
  4. customthe toluene layer was removed
  5. customevaporated in a rotary evaporator under vacuum

Sources & evidence

ORD record
ord-6cbb5b4bfd664254a9e8b69ce020987c
Source dataset
uspto-grants-2016_05
Patent number
US09353085B2

Reaction notes

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