Carbazole → HCID 22323475, compound

HRID 495871Notes

Reaction equation

HRID 495871 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH:7]1[C:19]2[NH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.C1OCCOCCOCCOCCOCCOC1.I[C:39]1[CH:40]=[C:41]([CH3:45])[CH:42]=[CH:43][CH:44]=1>ClC1C=CC=CC=1Cl>[CH3:45][C:41]1[CH:40]=[C:39]([N:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]3[C:19]2=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 122683-IodotolueneHCID 2855718-Crown-6

Product 1

HCID 22323475HCID 22323475, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Activated Cu, (4.2 g (65.8 mmol, 1.1 eq)), 12.4 g (89.7 mmol, 1.5 eq) of K2CO3, 10 g (59.8 mmol) of carbazole, 0.47 g (3 mol %) of 18-crown-6 and 13.7 g (62.8 mmol, 1.05 eq) of 3-iodotoluene were added into 100 ml of dried 1,2-dichlorobenzene and reacted at 180° C. for 24 hours. Then, the reaction mixture was filtered to remove un-reacted Cu and salts. The filtrate was distilled under reduced pressure to remove the solvent and purified by silica gel chromatography. The product was obtained as a colorless liquid at 88.3% (15.5 g) yield. 1H-NMR (300 MHz, CDCl3): δ 8.17 (2H, d), 7.51-7.27 (10H, m), 2.51 (3H, s).

Workup

  1. customreacted at 180° C. for 24 hours
  2. filtrationThen, the reaction mixture was filtered
  3. customto remove
  4. customun-reacted Cu and salts
  5. distillationThe filtrate was distilled under reduced pressure
  6. customto remove the solvent
  7. custompurified by silica gel chromatography
  8. customThe product was obtained as a colorless liquid at 88.3% (15.5 g)
  9. customyield

Sources & evidence

ORD record
ord-9e57623da43e4c038115758b964b7086
Source dataset
uspto-grants-2005_09
Patent number
US06942931B2

Reaction notes

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