Nitrogen → Biphenyl-4-yl-(12,12-dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-7-yl)amine

HRID 2275912Notes

Reaction equation

HRID 2275912 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]1[CH:9]=[C:8]3[C:21]([CH3:29])([CH3:28])[C:22]4[C:27]([C:7]3=[CH:6][C:5]2=1)=[CH:26][CH:25]=[CH:24][CH:23]=4.[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:33][CH:32]=1.N#N.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2].O>[C:34]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:33]=[CH:32][C:31]([NH:30][C:2]2[CH:3]=[C:4]3[C:12](=[CH:13][CH:14]=2)[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]2[CH:9]=[C:8]4[C:21]([CH3:29])([CH3:28])[C:22]5[C:27]([C:7]4=[CH:6][C:5]3=2)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:36][CH:35]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 71024-AminobiphenylHCID 23676156Sodium t-butoxideHCID 667976632-Bromo-7,7-dimethyl-5-phenyl-5,7-dihydroindeno[2,1-b]carbazole

Product 1

HCID 66798015Biphenyl-4-yl-(12,12-dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-7-yl)amine

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A degassed solution of 175 g (400 mmol) of 7-bromo-12,12-dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene and 67.7 g (401.8 mmol) of p-aminobiphenyl in 1000 ml of toluene is saturated with N2 for 1 h. 2.47 g (4.45 mmol) of 1,1-bis(diphenylphosphino)ferrocene and 1 g (4.45 mmol) of Pd(OAc)2 are then added to the solution, and 50.01 g (521.25 mmol) of NaOtBu in the solid state are subsequently added. The reaction mixture is heated under reflux for 5 h. After cooling to room temperature, 1000 ml of water are added. The organic phase is washed with 4×250 ml of H2O, then dried using MgSO4, and the solvent is removed under reduced pressure. The pure product is obtained by recrystallisation from dioxane as a colourless solid in a yield of 182 g (347 mmol), 87%.

Workup

  1. additionare subsequently added
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 5 h
  4. washThe organic phase is washed with 4×250 ml of H2O
  5. customdried
  6. customthe solvent is removed under reduced pressure
  7. customThe pure product is obtained by recrystallisation from dioxane as a colourless solid in a yield of 182 g (347 mmol), 87%

Sources & evidence

ORD record
ord-911f829e4a3d4c4cbe143e1de1551865
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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