8-Hydroxyquinoline → 1-Phenyl-1H-pyrrolo[3,2-b]pyridine

HRID 2039815Notes

Reaction equation

HRID 2039815 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O[C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1N=CC=C2.C(=O)([O-])[O-].[K+].[K+].IC1C=CC=CC=1.[OH-].[NH4+]>CS(C)=O.[Cu]I.CC(=O)OCC>[C:11]1([N:1]2[C:9]3[C:4](=[N:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:20]=1

Participants

9

Reactant 5

HCID 19238-HydroxyquinolineHCID 92264-AzaindoleHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 14923Ammonium Hydroxide

Product 1

HCID 210839631-Phenyl-1H-pyrrolo[3,2-b]pyridineYield 188.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of 4-azaindole (1.20 g, 10.2 mmol), copper(I) iodide (290 mg, 1.53 mmol), 8-hydroxyquinoline (221 mg, 1.53 mmol) and potassium carbonate (1.55 g, 11.2 mmol) in DMSO (24 ml) was added iodobenzene (1.25 ml, 11.2 mmol). The reaction mixture was stirred at 130° C. for 3 h. The mixture was then cooled to room temperature and a solution of ammonium hydroxide (10% in water) and EA were added. The organic layer was separated, washed twice with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. Column chromatography on silica gel (EA/HEP) gave 560 mg of the title compound.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed twice with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-81bb0f9394474220ae56e786b368d364
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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