Water → 1-(3-chloro-2-pyridinyl)-4-iodo-1H-pyrrole-2-carbaldehyde

HRID 251980Notes

Reaction equation

HRID 251980 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[CH:13]=[O:14])=[N:4][CH:5]=[CH:6][CH:7]=1.[I:15]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:1][C:2]1[C:3]([N:8]2[CH:12]=[C:11]([I:15])[CH:10]=[C:9]2[CH:13]=[O:14])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 587620783-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine

Product 1

HCID 577802671-(3-chloro-2-pyridinyl)-4-iodo-1H-pyrrole-2-carbaldehydeYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.0 g of 3-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine in 50 ml of N,N-dimethylformamide was added 5.4 g of N-iodosuccinimide. The resulting mixture was stirred at room temperature for 1 day. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate two times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.2 g of 1-(3-chloro-2-pyridinyl)-4-iodo-1H-pyrrole -2-carbaldehyde of the formula:

Workup

  1. extractionthe mixture was extracted with ethyl acetate two times
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-765b9601886547dc83e36589b8c503b0
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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