Benzene, 1,3-diiodo- → HCID 118112463, compound

HRID 924551Notes

Reaction equation

HRID 924551 reaction equation
[C:1]1([C:7]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[NH:26][C:25]3[N:30]=[CH:31][CH:32]=[CH:33][C:24]4=3)=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[CH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37](I)[CH:36]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[I:34][C:35]1[CH:36]=[C:37]([N:26]2[C:27]3[C:23](=[CH:22][C:21]([C:14]4[C:13]5[C:8]([C:7]([C:1]6[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=6)=[C:20]6[C:15]=4[CH:16]=[CH:17][CH:18]=[CH:19]6)=[CH:9][CH:10]=[CH:11][CH:12]=5)=[CH:29][CH:28]=3)[C:24]3[CH:33]=[CH:32][CH:31]=[N:30][C:25]2=3)[CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 12270Benzene, 1,3-diiodo-HCID 62657Potassium Phosphate, TribasicHCID 118112470HCID 118112470, compound

Product 1

HCID 118112463HCID 118112463, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

6-(10-phenylanthracen-9-yl)-9H-pyrido[2,3-b]indole (1.76 g, 4.19 mmol), 1,3-diiodobenzene (2.76 g, 8.37 mmol), CuI (319 mg, 1.67 mmol), K3PO4 (1.78 g, 8.37 mmol), trans-1,2-dicyclohexanediamine (0.2 mL, 1.67 mmol) were put in a 250 mL two-neck flask and dissolved in 1,4-dioxane. The solution was refluxed and stirred at 120° C. for 12 hours. After completion of the reaction, the solution was extracted with methylenechloride and H2O and was distilled under reduced pressure to remove the solvent. The resultant was columned with a solution of hexane and methylenechloride (1:5). The solution was re-crystallized in a solution of methylene chloride and petroleum ether such that the white solid compound was obtained, (1.66 g, yield: 63%).

Workup

  1. temperatureThe solution was refluxed
  2. customAfter completion of the reaction
  3. extractionthe solution was extracted with methylenechloride and H2O
  4. distillationwas distilled under reduced pressure
  5. customto remove the solvent
  6. customThe solution was re-crystallized in a solution of methylene chloride and petroleum ether such that the white solid compound
  7. customwas obtained

Sources & evidence

ORD record
ord-8e91105b5a164a4892d7b1566ebfe449
Source dataset
uspto-grants-2016_03
Patent number
US09281482B2

Reaction notes

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