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

HRID 524091Notes

Reaction equation

HRID 524091 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+) C8H8IN3 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-62033dadc19e4724b8a6d82ac76bf6b3
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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