Nitrogen → Bromo-8-phenyl-8H-8,12b-diazabenzo[a]aceanthrylene

HRID 2277347Notes

Reaction equation

HRID 2277347 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]3[C:19]4[C:18]([C:4]=2[CH:3]=1)=[CH:17][CH:16]=[CH:15][C:14]=4[NH:13][C:12]1[C:7]3=[CH:8][CH:9]=[CH:10][CH:11]=1.[C:22]1(N)[CH:27]=CC=[CH:24][CH:23]=1.N#N.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CC([O-])(C)C.[Na+].O1[CH2:55][CH2:54]OCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:1][C:2]1[C:3]2[N:6]3[C:19]4[C:18]([C:4]=2[CH:5]=[CH:20][CH:21]=1)=[CH:17][CH:16]=[CH:15][C:14]=4[N:13]([C:55]1[CH:54]=[CH:24][CH:23]=[CH:22][CH:27]=1)[C:12]1[C:7]3=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

9

Reactant 6

HCID 947NitrogenHCID 6115AnilineHCID 312751,4-DioxaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 673253603-Bromo-8H-8,12b-diazabenzo[a]aceanthrylene

Product 1

HCID 67325382Bromo-8-phenyl-8H-8,12b-diazabenzo[a]aceanthrylene

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

A degassed solution of 30 g (86.6 mmol) of 3-bromo-8H-8,12b-diazabenzo[a]aceanthrylene and 8.8 g (95.9 mmol) of phenylamine in 1000 ml dioxane is saturated with N2 for 1 h. Then firstly 0.9 ml (4.3 mmol) of P(tBu)3, then 0.48 g (2.1 mmol) of palladium(II) acetate are added to the solution, and 12.6 g (131 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 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.

Workup

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

Sources & evidence

ORD record
ord-224fd7b4751a4105b0f76b10e7fee648
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Reaction notes

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