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

HRID 2278467Notes

Reaction equation

HRID 2278467 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)=[N:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH:21]1[C:33]2[NH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:30]1[C:31]2[N:32]([C:2]3[CH:3]=[C:4]([C:8]4[O:9][C:10]([C:13]5[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=5)=[N:11][N:12]=4)[CH:5]=[CH:6][CH:7]=3)[C:33]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]=2[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 675117022-(3-Iodophenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

Product 1

HCID 675162742-(3-Carbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-iodophenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole (3.0 g, 7.93 mmol), carbazole (1.5 g, 8.97 mmol), Cu (2.0 g, 31.47 mmol) in DMF (20.0 ml) was added potassium carbonate (4.0 g, 28.94 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 dichloromethane/ethyl acetate (9.5:0.5) as eluent. After evaporating solvent, the white solid was recrystallized from acetone/methanol and finally dried under vacuum. Pure product was obtained as white solid in 3.15 g (95.4%) yield. 1H NMR (400 MHz, CDCl3, δ): 8.34 (m, 1H), 8.27 (m, 1 Hz), 8.18 (m, 2H), 7.78 (m, 2H), 7.71-7.65 (m, 2H), 7.46-7.41 (m, 5H), 7.36-7.31 (m, 2H), 7.09 (m, 1H), 3.89 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3, δ): 164.85, 163.84, 159.96, 140.60, 138.70, 130.85, 130.32, 130.25, 126.19, 125.84, 125.40, 124.72, 123.55, 120.45, 120.37, 119.39, 118.44, 111.52, 109.55, 55.55. [M]+ calcd for C39H26N4O2, 417.2. found 417.1.

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 acetone/methanol
  11. customfinally dried under vacuum
  12. customPure product was obtained as white solid in 3.15 g (95.4%)
  13. customyield

Sources & evidence

ORD record
ord-0f86b80b1a9f4bc5912c72649bb78959
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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