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

HRID 490273Notes

Reaction equation

HRID 490273 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]pyridineYield 88.4%

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 were initially charged together with 328 g (5.85 mol) of pulverulent KOH in 3000 ml of DMF and cooled to 0° C. A solution of 416 g (1.64 mol) of iodine in 3000 ml of DMF was added dropwise with cooling to this suspension and, on completion of addition, the suspension was stirred at 0° C. for a further 4 h. On completion of the reaction, the mixture was added to ice-water with stirring, and the solid formed was filtered off with suction and subsequently dried under high vacuum. A total of 403 g (1.45 mol, 88%) of 4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine were isolated as a colourless solid.

Workup

  1. temperaturewith cooling to this suspension and, on completion of addition
  2. customOn completion of the reaction
  3. stirringwith stirring
  4. customthe solid formed
  5. filtrationwas filtered off with suction
  6. customsubsequently dried under high vacuum

Sources & evidence

ORD record
ord-4163e486dc4d458180aa5431d9b59a8b
Source dataset
uspto-grants-2009_05
Patent number
US07528146B2

Reaction notes

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