Sodium Carbonate → 8,8-Dimethyl-3-(9-phenyl-9H-carbazol-3-yl)-8H-indolo-[3,2,1-de]acridine

HRID 2277352Notes

Reaction equation

HRID 2277352 reaction equation
[CH3:1][C:2]1([CH3:25])[C:15]2[C:10]3=[C:11]([C:16]4[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=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.Br[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:32]3[C:37]([C:38]=2[CH:39]=1)=[CH:36][CH:35]=[CH:34][CH:33]=3.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[CH3:1][C:2]1([CH3:25])[C:15]2[C:10]3=[C:11]([C:16]4[CH:17]=[C:18]([C:35]5[CH:34]=[CH:33][C:32]6[N:31]([C:40]7[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=7)[C:30]7[C:38]([C:37]=6[CH:36]=5)=[CH:39][CH:27]=[CH:28][CH:29]=7)[CH:19]=[CH:20][C:21]=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 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 189426243-Bromo-9-phenylcarbazoleHCID 672041848,8-Dimethyl-8H-indolo[3,2,1-de]acridine-3-boronic acid

Product 1

HCID 682336728,8-Dimethyl-3-(9-phenyl-9H-carbazol-3-yl)-8H-indolo-[3,2,1-de]acridine

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

36 g (110 mmol) of 8,8-dimethyl-8H-indolo[3,2,1-de]acridine-3-boronic acid, 35 g (110 mmol) of 3-bromo-9-phenyl-9H-carbazole and 9.7 g (92 mmol) of sodium carbonate are suspended in 350 ml of toluene, of dioxane and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and 112 mg (0.5 mmol) of palladium(II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene and from CH2Cl2/isopanol and finally sublimed in a high vacuum.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene and from CH2Cl2/isopanol

Sources & evidence

ORD record
ord-72d8740c7fbe4e2a9a01578444348e00
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Reaction notes

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