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

HRID 2274235Notes

Reaction equation

HRID 2274235 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-f6ead681766a42f38b2b6a4e69aec252
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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