N-Iodosuccinimide → 7-Chloro-3-iodo-1H-pyrrolo[2,3-c]pyridine

HRID 513204Notes

Reaction equation

HRID 513204 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.[I:11]N1C(=O)CCC1=O>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([I:11])=[CH:9][NH:8][C:7]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 114350487-Chloro-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 534131527-Chloro-3-iodo-1H-pyrrolo[2,3-c]pyridineYield 87.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 7-chloro-1H-pyrrolo[2,3-c]pyridine (0.75 g, 4.92 mmol) and N-iodo-succinimide (1.2 g, 5.41 mmol) was added acetonitrile (31 mL) and the solution was heated to 75 C. After 1 h, the mixture was cooled to r.t., the formed solid was filtered, washed with acetonitrile, and dried to yield the title product (1.2 g). HRMS (ESI) calc (M+H)+=278.9180. found 278.9181.

Workup

  1. temperaturethe solution was heated to 75 C
  2. filtrationthe formed solid was filtered
  3. washwashed with acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-05e985ae68c94ef9ad62258b38aeeac9
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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