N-Iodosuccinimide → 3-Iodo-imidazo[1,2-a]pyridine-8-carbonitrile

HRID 2404073Notes

Reaction equation

HRID 2404073 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[N:11])[C:5]=12.[I:12]N1C(=O)CCC1=O>ClCCl>[I:12][C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[N:11])[C:5]2=[N:1][CH:2]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 15098893Imidazo[1,2-a]pyridine-8-carbonitrile

Product 1

HCID 717572643-Iodo-imidazo[1,2-a]pyridine-8-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of imidazo[1,2-a]pyridine-8-carbonitrile (1.2 g, 8.38 mmol) in dichloromethane (10 mL) was added N-iodosuccinimide (1.89 g, 8.38 mmol). LCMS monitored the reaction until the starting material consumed completely. The reaction mixture was diluted with dichloromethane and water. The separated organic layer was dried sodium sulfate, filtered and concentrated to give 3-iodoimidazo[1,2-a]pyridine-8-carbonitrile (1.8 g, 6.69 mmol, 80% yield) as a brown solid. MS (ES+) C8H81N3 requires: 269. found: 270 [M+H]+.

Workup

  1. customthe reaction until the starting material
  2. customconsumed completely
  3. additionThe reaction mixture was diluted with dichloromethane and water
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1be97dbdfdfc4a988eb3b3be2dac7368
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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