Nitrogen → (8,8-Dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)diphenylamine

HRID 2277353Notes

Reaction equation

HRID 2277353 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[N:8]3[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:15]([CH3:23])([CH3:22])[C:14]4[C:9]3=[C:10]([CH:11]=[CH:12][CH:13]=4)[C:4]=2[CH:3]=1.[C:24]1([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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>[CH3:23][C:15]1([CH3:22])[C:16]2[C:21]3=[C:20]([C:4]4[CH:3]=[C:2]([N:30]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)[C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH:7]=[CH:6][C:5]=4[N:8]3[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]1=3)[CH:19]=[CH:18][CH:17]=2

Participants

9

Reactant 5

HCID 947NitrogenHCID 11487DiphenylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 671095853-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

Product 1

HCID 67325570(8,8-Dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)diphenylamine

Reagents, catalysts & solvents 3

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

Procedure

A degassed solution of 31 g (86.6 mmol) of 3-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine and 16 g (95.9 mmol) of diphenylamine in 1000 ml of 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 and final sublimation.

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-d6721943aaec4b88885024f17b53b011
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Reaction notes

Loading…