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

HRID 1396130Notes

Reaction equation

HRID 1396130 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 an atmosphere or nitrogen, pyridine (7.951 mL, 98.31 mmol) and iodine monochloride (110 mL, 1.0 M in dichloromethane, 110 mmol) are added slowly over 20 minutes. The reaction is stirred at room temperature for 2 hours, then quenched with 100 mL of 1 M aqueous sodium thiosulfate pentahydrate. The layers are separated, solids collected from the aqueous layer by filtration and combined with the organic layer. The aqueous layer is extracted with ethyl acetate, and the organic layers are combined and washed with brine, then concentrated under vacuum. The resulting solid is washed with 20% ethyl acetate in hexane to provide the desired compound.

Workup

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

Sources & evidence

ORD record
ord-ab3cbc7676364e108e7e86bf5829968e
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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