5-(2-Aminophenylethynyl)-2,4-dimethoxybenzaldehyde → 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

HRID 347383Notes

Reaction equation

HRID 347383 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]#[C:9][C:10]1[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14]([CH:17]=1)[CH:15]=[O:16]>C(#N)C.Cl[Pd]Cl>[NH:1]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:8]=[C:9]1[C:10]1[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14]([CH:17]=1)[CH:15]=[O:16]

Participants

4

Reactant 1

HCID 161156205-(2-Aminophenylethynyl)-2,4-dimethoxybenzaldehyde

Product 1

HCID 161156215-(1H-indol-2-yl)-2,4-dimethoxybenzaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of PdCl2 (0.066 g, 0.373 mmol) in 200 ml of acetonitrile was heated to reflux. To this solution was added 5-(2-amino-phenylethynyl)-2,4-dimethoxybenzaldehyde (Ex-35C, 1.4 g, 5 mmol) portion by portion slowly so that no cloudiness of the solution occurred. After the addition, the reaction was kept at reflux for another 10 min. Then the mixture was cooled to room temperature and filtered. The filtrate was treated with 5 g of 3-mercaptopropyl functional silica gel with stirring for 30 min and filtered. The filtrate was concentrated and the residue was recrystallized from EtOAc/Hexane to give 0.84 g (60%) of 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde, analytical dada identical as in Ex-57D.

Workup

  1. additionAfter the addition
  2. temperatureat reflux for another 10 min
  3. filtrationfiltered
  4. additionThe filtrate was treated with 5 g of 3-mercaptopropyl functional silica gel
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was recrystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-6012d6b30af64b9ca756836885894188
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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