Dimethylformamide → 1-(2-Iodobenzoyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde

HRID 433067Notes

Reaction equation

HRID 433067 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]#N)[C:6]([N+:12]([O-])=O)=[CH:5][CH:4]=1.[H-].[Na+].[I:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].CN([CH:30]=[O:31])C>>[I:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([N:12]1[C:6]2[C:7](=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]([CH:30]=[O:31])=[CH:10]1)=[O:21]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 691122-Iodobenzoyl chlorideHCID 6395106-Methoxy-3-nitropyridine-2-acetonitrile

Product 1

HCID 187582411-(2-Iodobenzoyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 0.56 mmol of the compound obtained in Step A are dissolved in 5 ml of DMF, and then 0.68 mmol of NaH are added at 0° C., over a period of 30 minutes. After 30 minutes' stirring at 0° C., 0.68 mmol of 2-iodobenzoyl chloride dissolved in 5 ml of DMF is added dropwise to the mixture. After 3 hours' stirring, the solvents are removed by evaporation and the residue is taken up in water and extracted with dichloromethane. After drying over magnesium sulphate and removal of the solvents by evaporation, the residue is purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate) to yield the title compound.

Workup

  1. additionis added dropwise to the mixture
  2. stirringAfter 3 hours' stirring
  3. customthe solvents are removed by evaporation
  4. extractionextracted with dichloromethane
  5. dry with materialAfter drying over magnesium sulphate and removal of the solvents by evaporation
  6. customthe residue is purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-0ef1ca36a1514b65987adfd4ee1c2dc6
Source dataset
uspto-grants-2003_12
Patent number
US06667304B2

Reaction notes

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