Tris(1,1-dimethylethyl)phosphine → 7-(3,6-Diphenylcarbazol-9-yl)-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275926Notes

Reaction equation

HRID 2275926 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:16]=1)[C:10]1[CH:9]=[C:8]3[C:33]([CH3:41])([CH3:40])[C:34]4[C:39]([C:7]3=[CH:6][C:5]2=1)=[CH:38][CH:37]=[CH:36][CH:35]=4.[C:42]1([C:48]2[CH:49]=[CH:50][C:51]3[NH:52][C:53]4[C:58]([C:59]=3[CH:60]=2)=[CH:57][C:56]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[CH:55][CH:54]=4)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>CC1C=CC(C)=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:42]1([C:48]2[CH:49]=[CH:50][C:51]3[N:52]([C:2]4[CH:3]=[C:4]5[C:12](=[CH:13][CH:14]=4)[N:11]([C:15]4[N:20]=[C:19]([C:21]6[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=6)[N:18]=[C:17]([C:27]6[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=6)[N:16]=4)[C:10]4[CH:9]=[C:8]6[C:33]([CH3:40])([CH3:41])[C:34]7[C:39]([C:7]6=[CH:6][C:5]5=4)=[CH:38][CH:37]=[CH:36][CH:35]=7)[C:53]4[C:58]([C:59]=3[CH:60]=2)=[CH:57][C:56]([C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)=[CH:55][CH:54]=4)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 31232953,6-DiphenylcarbazoleHCID 667979517-Bromo-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Product 1

HCID 667980397-(3,6-Diphenylcarbazol-9-yl)-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

20 g (33.7 mmol) of 7-bromo-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene, 12 g (37.6 mmol) of 3,6-diphenyl-9H-carbazole and 23.34 g of Rb2CO3 are suspended in 200 ml of p-xylene. 0.76 g (3.4 mmol) of Pd(OAc)2 and 10.1 ml of a 1 M tri-tert-butylphosphine solution are added to this suspension. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is extracted with hot toluene, recrystallised from toluene and finally sublimed in a high vacuum, the purity is 99.9%. Yield: 20 g (24 mmol), 72% of theory.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed three times with 200 ml of water
  6. customsubsequently evaporated to dryness
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised from toluene

Sources & evidence

ORD record
ord-d7b73814c3ac42df8839f373b4033b62
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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