Nitrogen → [4'-(8,12b-Diazabenzo[a]aceanthrylen-8-yl)biphenyl-4-yl]diphenylamine

HRID 2277358

Reaction equation

HRID 2277358 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH:27]1[C:32]2[N:33]3[C:46]4[C:45]([C:31]=2[CH:30]=[CH:29][CH:28]=1)=[CH:44][CH:43]=[CH:42][C:41]=4[NH:40][C:39]1[C:34]3=[CH:35][CH:36]=[CH:37][CH:38]=1.N#N.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CC([O-])(C)C.[Na+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:27]1[C:32]2[N:33]3[C:46]4[C:45]([C:31]=2[CH:30]=[CH:29][CH:28]=1)=[CH:44][CH:43]=[CH:42][C:41]=4[N:40]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[C:39]1[C:34]3=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

9

Reactant 5

HCID 947NitrogenHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 113155504-Bromo-4'-(diphenylamino)biphenylHCID 23676156Sodium t-butoxideHCID 671105678H-8,12b-Diazabenzo[a]aceanthrylene

Product 1

HCID 67324186[4'-(8,12b-Diazabenzo[a]aceanthrylen-8-yl)biphenyl-4-yl]diphenylamine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A degassed solution of 35.6 g (89 mmol) of (4′-bromobiphenyl-4-yl)-diphenylamine and 22.0 g (81 mmol) of 8H-8,12b-diazabenzo[a]aceanthrylene in 1000 ml of dioxane is saturated with N2 for 1 h. Then firstly 1.0 ml (4 mmol) of P(tBu)3, then 0.4 g (2 mmol) of palladium(II) acetate are added to the solution, and 11.7 g (122 mmol) of NaOtBu in the solid state are subsequently added. The reaction mixture is heated under reflux for 18 h. After cooling to room temperature, 1000 ml of water are carefully added. The organic phase is separated off, washed with 4×50 ml of water and dried over MgSO4, and the solvent is removed in vacuo. The pure product is obtained by recrystallisation and final sublimation in a high vacuum.

Workup

  1. additionare subsequently added
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 18 h
  4. customThe organic phase is separated off
  5. washwashed with 4×50 ml of water
  6. dry with materialdried over MgSO4
  7. customthe solvent is removed in vacuo
  8. customThe pure product is obtained by recrystallisation

Sources & evidence

ORD record
ord-ecf6fc362d3a484090a4aaeee18f7bf1
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Linked notes

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