Ethanol → HCID 71268869, compound

HRID 530766Notes

Reaction equation

HRID 530766 reaction equation
[C:1]([N:4]1[C:16]2[CH:15]=[CH:14][C:13](Br)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[CH3:2].[S:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=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>[C:1]([N:4]1[C:16]2[CH:15]=[CH:14][C:13]([C:30]3[CH:31]=[CH:32][C:27]([C:19]4[S:18][C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=5[N:20]=4)=[CH:28][CH:29]=3)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 17148799-Acetyl-3-bromocarbazoleHCID 57655345HCID 57655345, compound

Product 1

HCID 71268869HCID 71268869, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 5.8 g of 9-Acetyl-3-bromocarbazole and 5.7 g of (4-benzo[d]thiazol-2-yl) phenylboronic acid were stirred together in 30 ml of toluene. To this was added 0.03 g of tetrakis(triphenylphosphine)palladium, 4.2 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 6.7 g of 9-acetyl-3-[(4-benzo [d]thiazol-2-yl) phenyl]-9H-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-6111159476804ddeb7c2da60de5b544e
Source dataset
uspto-grants-2016_05
Patent number
US09353085B2

Reaction notes

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