Iodine chloride → 3-Iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 509927Notes

Reaction equation

HRID 509927 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.[I:12]Cl>ClCCl>[I:12][C:11]1[C:5]2[C:6](=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 103078715-methoxy-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 242292443-Iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridineYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-1H-pyrrolo[2,3-b]pyridine (14, 300 mg, 2.0 mmol) in 30 mL of dichloromethane under nitrogen, iodine monochloride (3 mL, 1.0 M in dichloromethane, 3.0 mmol) was added at −40° C. The reaction was stirred to room temperature, then quenched with 10 mL of 1 M aqueous sodium thiosulfate pentahydrate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and washed with water, brine, then dried over sodium sulfate, decolored with activated carbon, filtered and the filtrate concentrated under vacuum. The resulting solid was washed with 20% ethyl acetate in hexane to provide the desired compound (15, 371 mg). MS (ESI) [M+H+]+=275.03.

Workup

  1. customquenched with 10 mL of 1 M aqueous sodium thiosulfate pentahydrate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. washThe resulting solid was washed with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5ce2312f28634aaabc77de574192c40c
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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