Carbazole → 2-(3,5-Dicarbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

HRID 2278472Notes

Reaction equation

HRID 2278472 reaction equation
I[C:2]1[CH:3]=[C:4]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)=[N:12][N:13]=2)[CH:5]=[C:6](I)[CH:7]=1.[CH:22]1[C:34]2[NH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:31]1[C:32]2[N:33]([C:2]3[CH:3]=[C:4]([C:9]4[O:10][C:11]([C:14]5[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=5)=[N:12][N:13]=4)[CH:5]=[C:6]([N:33]4[C:34]5[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=5[C:27]5[C:32]4=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:7]=3)[C:34]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]=2[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 675109952-(3,5-Diiodophenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

Product 1

HCID 675114452-(3,5-Dicarbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3,5-diiodophenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole (1.0 g, 1.98 mmol), carbazole (1.0 g, 5.98 mmol), Cu (4.0 g, 62.95 mmol) in DMF (20.0 ml) was added potassium carbonate (6.0 g, 43.41 mmol) under nitrogen and stirring. Heating was started. The reaction was carried out at 150° C. for 5 h. After cooling, the reaction mixture was filtrated. The solid residues were carefully washed with THF. THF was evaporated from the combined filtration solution. Water (150.0 ml) was added, the brown solid product was obtained by filtration. The crude product was purified by silica gel column chromatography using toluene/ethyl acetate (9.7:0.3) as eluent. After evaporating solvent, the white solid was recrystallized from THF/methanol and finally dried under vacuum. Pure product was obtained as white solid in 0.99 g (86.0%) yield. 1H NMR (399 MHz, CDCl3, δ): 8.47 (d, J=2.4 Hz, 2H), 8.16 (d, J=8.0 Hz, 4 Hz), 8.01 (t, J=1.6 Hz, 1H), 7.69-7.64 (m, 2H), 7.58 (d, J=8.0 Hz, 4H), 7.45 (m, 4H), 7.41 (t, J=8.0 Hz, 1H), 7.34 (m, 4H), 7.08 (m, 1H), 3.87 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3, δ): 164.72, 164.02, 159.99, 140.90, 140.21, 130.28, 128.58, 127.21, 126.21, 124.88, 123.76, 122.40, 120.57, 120.48, 119.33, 118.29, 111.61, 109.68, 94.23, 55.55. [M]+ calcd for C39H26N4O2, 582.2. found 582.2. Anal. Calcd for C39H26N4O2: C, 80.39; H, 4.50; N, 9.62. Found: C, 80.32; H, 4.41; N, 9.60.

Workup

  1. temperatureHeating
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtrated
  4. washThe solid residues were carefully washed with THF
  5. customTHF was evaporated from the combined filtration solution
  6. additionWater (150.0 ml) was added
  7. customthe brown solid product was obtained by filtration
  8. customThe crude product was purified by silica gel column chromatography
  9. customAfter evaporating solvent
  10. customthe white solid was recrystallized from THF/methanol
  11. customfinally dried under vacuum
  12. customPure product was obtained as white solid in 0.99 g (86.0%)
  13. customyield

Sources & evidence

ORD record
ord-4c760af73b374f6eaef1e3a48e411fc1
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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