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

HRID 729784Notes

Reaction equation

HRID 729784 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 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a 500 mL round bottomed flask were added 5-bromo-1H-pyrrolo[2,3-b]pyridine (10.11 g, 51.3 mmol) and 250 ml acetone. N-iodosuccinimide (NIS, 12.7 g, 56.4 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. The precipitate was collected and washed with cold acetone to afford 12.2 g (74%) of the title compound as a tan powder. 1H-NMR (500 MHz, d6-DMSO) δ=12.35 (br.s, 1H), 8.29 (d, J=2.0 Hz, 1H), 7.84 (d, J=2.0 Hz 1H), 7.79 (s, 1H); MS: m/z 322.8/324.8 [MH+].

Workup

  1. customThe precipitate was collected
  2. washwashed with cold acetone

Sources & evidence

ORD record
ord-7dfd97a90ad9417db2cbee859d7759ee
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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