N-Iodosuccinimide → 5-Bromo-3-iodo-1H-pyrrolo(2,3-b)pyridine

HRID 901389Notes

Reaction equation

HRID 901389 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.[I:11]N1C(=O)CCC1=O>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 242292125-Bromo-3-iodo-1H-pyrrolo(2,3-b)pyridineYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (300 mg, 1.52 mmol) in acetone (10 ml) was added N-iodosuccinimide (377 mg, 1.67 mmol) in one portion. The reaction mixture was stirred at room temperature for 45 minutes. The resulting precipitate was filtered off, washed with a minimal amount of acetone, and dried in vacuo to give the title compound as a cream-colored solid (329 mg, 67% yield). 1H NMR (DMSO-d6): δ 12.36 (s, 1H), 8.30 (d, J=2.0 Hz, 1H), 7.85 (d, J=2.0 Hz, 1H), 7.80 (d, J=2.5 Hz, 1H); HPLC/MS m/z: 323.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with a minimal amount of acetone
  3. customdried in vacuo

Sources & evidence

ORD record
ord-872da7bcc73a425cb7f273cbd61f9317
Source dataset
uspto-grants-2008_04
Patent number
US07361763B2

Reaction notes

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