Potassium Hydroxide → 5-Bromo-3-iodo-1H-pyrrolo(2,3-b)pyridine

HRID 63595Notes

Reaction equation

HRID 63595 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[K+].[I:13]N1C(=O)CCC1=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[I:13][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[NH:8][CH:9]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 242292125-Bromo-3-iodo-1H-pyrrolo(2,3-b)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-1H-pyrrolo[2,3-b]-pyridine (commercial product, 1 g, 5.10 mmol) in 200 ml of CH2Cl2 is added KOH (145 mg, 2.55 mmol) at room temperature. After 30 minutes, N-iodosuccinimide (1.2 g, 5.10 mmol) is added and the solution is stirred for 15 hours, neutralized with saturated Na2S2O3 solution and extracted several times with CH2Cl2. The organic phases are combined, dried on MgSO4 and concentrated under reduced pressure. The expected product is obtained with a quantitative yield and used in the following step without additional purification.

Workup

  1. extractionextracted several times with CH2Cl2
  2. customdried on MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96d829c812d74501a86acdbdb74a4796
Source dataset
uspto-grants-2016_09
Patent number
US09447093B2

Reaction notes

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