Iodine → 4-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 2240254Notes

Reaction equation

HRID 2240254 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[OH-].[K+].[I:13]I>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[C:10]([I:13])[C:3]=12

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 115508744-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

250 g (1.64 mol) of 4-chloro-1H-pyrrolo[2,3-b]pyridine and 328 g (5.85 mol) of powdered potassium hydroxide are initially charged in 3000 ml of DMF and cooled to 0° C. With cooling, a solution of 416 g (1.64 mol) of iodine in 3000 ml of DMF is added dropwise to this suspension, and the mixture is, after the end of the addition, stirred at 0° C. for 4 h. To bring the reaction to completion, the mixture is added with stirring to ice-water and the solid formed is filtered off with suction and then dried under high vacuum. This gives 403 g (88% of theory) of the title compound as a solid.

Workup

  1. temperatureWith cooling
  2. additionafter the end of the addition
  3. customthe reaction to completion
  4. additionthe mixture is added
  5. customthe solid formed
  6. filtrationis filtered off with suction
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-661ca6416cd3480ba689c578e1da7ba1
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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