N-Iodosuccinimide → 7-Bromo-3-chloro-8-iodoisoquinoline

HRID 1465751Notes

Reaction equation

HRID 1465751 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([Cl:12])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.C1C(=O)N([I:20])C(=O)C1>S(O)(C(F)(F)F)(=O)=O>[Br:1][C:2]1[C:11]([I:20])=[C:10]2[C:5]([CH:6]=[C:7]([Cl:12])[N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 513419807-Bromo-3-chloroisoquinoline

Product 1

HCID 895252237-Bromo-3-chloro-8-iodoisoquinoline

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

To a flask containing 7-Bromo-3-chloroisoquinoline (1.5 g, 6.19 mmol) was added NIS (1.4 g, 6.9 mmol). The flask was placed in an ice bath and treated with TfOH (40 mL) and stirred at RT overnight. The reaction mixture was carefully poured into ice, and the aqueous layer was extracted with DCM. The combined extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (Hexanes:DCM→1:1) to provide the title product.

Workup

  1. customThe flask was placed in an ice bath
  2. additionThe reaction mixture was carefully poured into ice
  3. extractionthe aqueous layer was extracted with DCM
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by silica gel column chromatography (Hexanes:DCM→1:1)

Sources & evidence

ORD record
ord-ed496408991d4f62b8fd0a4513bf584d
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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