Pyridine → 5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 509921Notes

Reaction equation

HRID 509921 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.N1C=CC=CC=1.[I:17]Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([I:17])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24640Iodine chlorideHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 242292205-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-1H-pyrrolo[2,3-b]pyridine (1, 15.00 g, 98.31 mmol) in 300 mL of dichloromethane under nitrogen, pyridine (7.951 mL, 98.31 mmol) and iodine monochloride (110 mL, 1.0 M in dichloromethane, 110 mmol) were added slowly over 20 minutes. The reaction was stirred at room temperature for 2 hours, then quenched with 100 mL of 1 M aqueous sodium thiosulfate pentahydrate. The layers were separated, solids collected from the aqueous layer by filtration and combined with the organic layer. The aqueous layer was extracted with ethyl acetate, organic layers were combined and washed with brine, then concentrated under vacuum. The resulting solid was washed with 20% ethyl acetate in hexane to provide the desired compound. 5-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine is prepared similarly from 5-fluoro-1H-pyrrolo[2,3-b]pyridine.

Workup

  1. customquenched with 100 mL of 1 M aqueous sodium thiosulfate pentahydrate
  2. customThe layers were separated
  3. filtrationsolids collected from the aqueous layer by filtration
  4. extractionThe aqueous layer was extracted with ethyl acetate, organic layers
  5. washwashed with brine
  6. concentrationconcentrated under vacuum
  7. washThe resulting solid was washed with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8061cae26e264945a3468a0ed4a26165
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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