N-Iodosuccinimide → 2-bromo-7-iodo-5H-pyrrolo(2,3-b)pyrazine

HRID 85027Notes

Reaction equation

HRID 85027 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1.[I:11]N1C(=O)CCC1=O>CC(C)=O>[Br:1][C:2]1[N:7]=[C:6]2[C:8]([I:11])=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 441182772-bromo-7-iodo-5H-pyrrolo(2,3-b)pyrazineYield 89.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-bromo-5H-pyrrolo[3,2-b]pyrazine [Intermediate AS] (0.68 g, 3.4 mmol) in acetone (17 mL) was added N-iodosuccinimide (0.82 g, 3.6 mmol) and the resulting mixture was stirred for 4 h at rt. The mixture was evaporated in vacuo to yield a residue that was purified via silica gel chromatography eluting with 40% THF in hexanes to give the title compound as a yellow solid (0.99 g, 89%). 1H NMR (DMSO-d6, 300 MHz): δ 12.82 (s, 1H), 8.42 (s, 1H), 8.20 (s, 1H). HPLC retention time: 2.23 minutes. MS ESI (m/z): 324.0, 326.0 (M+H)+, calc. 323.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto yield a residue that
  3. customwas purified via silica gel chromatography
  4. washeluting with 40% THF in hexanes

Sources & evidence

ORD record
ord-5e3867ce7af54d15ba28d0435e58c40d
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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