9,9-Dimethyl-9H-fluoren-2-amine → 9,9-Dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

HRID 1530741Notes

Reaction equation

HRID 1530741 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:13]4[C:18]([C:19]=3[CH:20]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:4][CH:3]=1.[CH3:27][C:28]1([CH3:42])[C:40]2[CH:39]=[C:38]([NH2:41])[CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2>C1(C)C=CC=CC=1>[CH3:27][C:28]1([CH3:42])[C:40]2[CH:39]=[C:38]([NH:41][C:2]3[CH:3]=[CH:4][C:5]([C:8]4[CH:9]=[CH:10][C:11]5[N:12]([C:21]6[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=6)[C:13]6[C:18]([C:19]=5[CH:20]=4)=[CH:17][CH:16]=[CH:15][CH:14]=6)=[CH:6][CH:7]=3)[CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2

Participants

4

Reactant 2

HCID 226170939,9-Dimethyl-9H-fluoren-2-amineHCID 667163243-(4-Iodo-phenyl)-9-phenyl-9H-carbazole

Product 1

HCID 580508019,9-Dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amineYield 96.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 g (112 mmol) 3-(4-Iodo-phenyl)-9-phenyl-9H-carbazole and 23.5 g (112 mmol) 9,9-Dimethyl-9H-fluoren-2-ylamine are dissolved in 500 ml toluene and 21.5 g sodium-tert-butylat is added. The reaction mixture is carefully degassed and 80 mg bis(diphenylphosphino)ferrocendichloro-Pd(II) (Pd(dppf)) complex is added. The solution is refluxed for 6 h. The reaction mixture is then cooled to room temperature and 250 ml water are added. The layers are separated. The water phase is extracted three times with toluene, and then the organic layers is washed twice with water dried over magnesium sulphate, filtrated and the solvent is removed under vacuum. The residue is recrystallized from butanole, to yield 57 g (108 mmol) (96%) of a white solid with a purity of 99.5%.

Workup

  1. customThe reaction mixture is carefully degassed
  2. addition80 mg bis(diphenylphosphino)ferrocendichloro-Pd(II) (Pd(dppf)) complex is added
  3. temperatureThe solution is refluxed for 6 h
  4. addition250 ml water are added
  5. customThe layers are separated
  6. extractionThe water phase is extracted three times with toluene
  7. washthe organic layers is washed twice with water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltrated
  10. customthe solvent is removed under vacuum
  11. customThe residue is recrystallized from butanole

Sources & evidence

ORD record
ord-a644592c60004443bd7b127227f1ad7a
Source dataset
uspto-grants-2015_07
Patent number
US09093656B2

Reaction notes

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