Potassium Carbonate → 2'-(1H-pyrazol-1-yl)-9-(pyridin-2-yl)-9H-2,9'-bicarbazole

HRID 591585Notes

Reaction equation

HRID 591585 reaction equation
[N:1]1([C:6]2[CH:18]=[CH:17][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[NH:9][C:8]=3[CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.Br[C:20]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[C:22]=2[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>[Cu]I>[N:1]1([C:6]2[CH:18]=[CH:17][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]([C:20]4[CH:32]=[CH:31][C:30]5[C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[N:23]([C:33]6[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=6)[C:22]=5[CH:21]=4)[C:8]=3[CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 706548522-bromo-9-(pyridin-2-yl)-9H-carbazoleHCID 710602702-(1H-pyrazol-1-yl)-9H-carbazole

Product 1

HCID 710604562'-(1H-pyrazol-1-yl)-9-(pyridin-2-yl)-9H-2,9'-bicarbazoleYield 60%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, 10 mmol of 2-(1H-pyrazol-1-yl)-9H-carbazole, 10 mmol of 2-bromo-9-(pyridin-2-yl)-9H-carbazole, 1 mmol of copper(I)iodide, 25 mmol of potassium carbonate, and 2 mmol of L-proline were combined in stirring degassed dimethyl sulfoxide. The mixture was heated to 90° C. for 3 days before being cooled and separated between dichloromethane and water. The water layer was washed twice with dichloromethane and the organics were combined and washed once with brine. The organic fraction was dried with magnesium sulfate and concentrated under reduced pressure and subjected to column chromatography of silica with dichloromethane/ethyl acetate as the eluent. After concentrating under reduced pressure, 2′-(1H-pyrazol-1-yl)-9-(pyridin-2-yl)-9H-2,9′-bicarbazole was isolated in a 60% yield.

Workup

  1. customdegassed dimethyl sulfoxide
  2. temperaturebefore being cooled
  3. customseparated between dichloromethane and water
  4. washThe water layer was washed twice with dichloromethane
  5. washwashed once with brine
  6. dry with materialThe organic fraction was dried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. concentrationAfter concentrating under reduced pressure

Sources & evidence

ORD record
ord-2f1e30e93aea45c69aacf49e48edc458
Source dataset
uspto-grants-2016_01
Patent number
US09238668B2

Reaction notes

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