9-Acetyl-3-bromocarbazole → 3-(N-phenyindolo[2,3-a]carbazolyl)carbazole

HRID 2045741Notes

Reaction equation

HRID 2045741 reaction equation
C([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)C.[C:18]1([N:24]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]4[C:43]5[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=5[NH:37][C:35]4=3)[C:30]3[C:25]2=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Cu]=O>[C:18]1([N:24]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]4[C:43]5[CH:42]=[CH:41][CH:40]=[C:39]([C:8]6[CH:7]=[CH:6][C:5]7[NH:4][C:16]8[C:11]([C:10]=7[CH:9]=6)=[CH:12][CH:13]=[CH:14][CH:15]=8)[C:38]=5[NH:37][C:35]4=3)[C:30]3[C:25]2=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 17148799-Acetyl-3-bromocarbazoleHCID 5936587111,12-Dihydro-11-phenylindolo[2,3-a]carbazole

Product 1

HCID 1317310533-(N-phenyindolo[2,3-a]carbazolyl)carbazoleYield 84%

Reagents, catalysts & solvents 1

HCID 14829Copper oxideCatalyst

Conditions

Temperature
170 °C

Procedure

A mixture of 2.0 g of 9-acetyl-3-bromocarbazole prepared as described above and 2.4 g of N-phenylindolo[2,3-a]carbazole (IC-1) were stirred together in 20 ml N,N′-dimethylacetamide. To this was added 0.8 g of copper oxide and heated to 170° C. for 24 h. The reaction was quenched with water and the solid was filtered, washed with methanol, and dried under vacuum. The solid (4.5 g) was then taken up for further deprotection using 0.8 g KOH with THF (4 ml), methanol (8 ml) and water (8 ml) at reflux temperature. The reaction mixture was then extracted using ethylacetate; and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. Subsequent silica gel column chromatography using toluene:hexane (1:2) as eluent, yielded 2.9 g of 3-(N-phenyindolo[2,3-a]carbazolyl)carbazole as a light yellow solid.

Workup

  1. customprepared
  2. customThe reaction was quenched with water
  3. filtrationthe solid was filtered
  4. washwashed with methanol
  5. customdried under vacuum
  6. temperatureat reflux temperature
  7. extractionThe reaction mixture was then extracted
  8. dry with materialand the organic layer was dried over anhydrous sodium sulfate
  9. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-347b7a339e9c40baa155ee5be194f47b
Source dataset
uspto-grants-2013_11
Patent number
US08592055B2

Reaction notes

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