1,5-Dichloroanthraquinone → HCID 59229125, compound

HRID 1019488Notes

Reaction equation

HRID 1019488 reaction equation
CC(C)([O-])C.[K+].[CH3:7][CH:8]([CH2:10][N:11]1P2N(CC(C)C)CC[N:14](CCN2CC(C)C)[CH2:13][CH2:12]1)C.[NH2:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1.Cl[C:38]1[C:51]2[C:50](=[O:52])[C:49]3[C:44](=[C:45](Cl)[CH:46]=[CH:47][CH:48]=3)[C:43](=[O:54])[C:42]=2[CH:41]=[CH:40][CH:39]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[N:33]1[CH:34]=[CH:35][CH:36]=[C:31]([NH:30][C:38]2[C:51]3[C:50](=[O:52])[C:49]4[C:44](=[C:45]([NH:14][C:13]5[CH:12]=[N:11][CH:10]=[CH:8][CH:7]=5)[CH:46]=[CH:47][CH:48]=4)[C:43](=[O:54])[C:42]=3[CH:41]=[CH:40][CH:39]=2)[CH:32]=1

Participants

7

Reactant 4

HCID 67111,5-DichloroanthraquinoneHCID 100093-AminopyridineHCID 45712432,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 59229125HCID 59229125, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Potassium t-butoxide (3.37 g, 30 mmol) and Pd2(dba)3 (0.55 g, 0.6 mmol) were added to a 100 mL round bottom flask. Toluene (50 mL) and triisobutylphosphatrane (0.82 g, 2.4 mmol) were then added, followed by 3-aminopyridine (1.88 g, 20 mmol) and 1,5-dichloroanthraquinone (2.77 g, 10 mmol). The system was flushed with argon and heated to reflux overnight. The mixture was cooled and the solvent was removed under vacuum. The residue was dissolved in dichloromethane and water. The organic layer was washed with water twice and dried over anhydrous magnesium sulfate. After the solvent was removed, the residue was purified by flash chromatography to provide Compound 27 as a red solid. The structure of Compound 27 is given below:

Workup

  1. customThe system was flushed with argon
  2. temperatureheated
  3. temperatureto reflux overnight
  4. temperatureThe mixture was cooled
  5. customthe solvent was removed under vacuum
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washThe organic layer was washed with water twice
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter the solvent was removed
  10. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7c11f9fc3fce4a399e353b257f764c6d
Source dataset
uspto-grants-2014_05
Patent number
US08715944B2

Reaction notes

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