Nitrogen → Dimethyl 2-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-2-yl)-5-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)terephthalate

HRID 1485593Notes

Reaction equation

HRID 1485593 reaction equation
[CH3:1][C:2]1([CH3:25])[C:15]2[C:10]3=[C:11]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[N:9]3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=3)[CH:12]=[C:13](B(O)O)[CH:14]=2.Br[C:27]1[C:28](Br)=[C:29]([CH:35]=[CH:36][C:37]=1[C:38]([O:40][CH2:41]C)=[O:39])[C:30]([O:32][CH2:33]C)=[O:31].C(=O)([O-])[O-].[K+].[K+].N#N>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO>[CH3:1][C:2]1([CH3:25])[C:15]2[C:10]3=[C:11]([C:19]4[CH:20]=[CH:21][C:22]([C:35]5[CH:36]=[C:37]([C:38]([O:40][CH3:41])=[O:39])[C:27]([C:21]6[CH:22]=[CH:23][C:24]7[N:9]8[C:8]9[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=9[C:2]([CH3:25])([CH3:1])[C:15]9[C:10]8=[C:11]([CH:12]=[CH:13][CH:14]=9)[C:19]=7[CH:20]=6)=[CH:28][C:29]=5[C:30]([O:32][CH3:33])=[O:31])=[CH:23][C:24]=4[N:9]3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=3)[CH:12]=[CH:13][CH:14]=2

Participants

9

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 66645638Diethyl dibromoterephthalateHCID 673261988,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

Product 1

HCID 67452042Dimethyl 2-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-2-yl)-5-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)terephthalate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

268 g (820 mol) of 8,8-dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid, 180.4 g (474 mmol) of diethyl dibromoterephthalate and 315.9 g (2.29 mol) of potassium carbonate are initially introduced in a mixture of 850 ml of toluene and 850 ml of water and saturated with N2 for 30 min. After addition of 1.36 g (1.18 mmol) of Pd(PPh3)4, the mixture is heated at the boil for 4 h. After cooling to RT and addition of 400 ml of EtOH, the mixture is cooled to room temperature and stirred for 1 h, and the precipitate is filtered off with suction, washed with water, EtOH and heptane and dried at 80° C. in vacuo. The yield is 295 g (390 mmol), corresponding to 71% of theory.

Workup

  1. temperaturethe mixture is heated at the boil for 4 h
  2. temperaturethe mixture is cooled to room temperature
  3. filtrationthe precipitate is filtered off with suction
  4. washwashed with water, EtOH and heptane
  5. customdried at 80° C. in vacuo

Sources & evidence

ORD record
ord-2ad2e3e6899d40bc80123bcae568f5fa
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

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