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

HRID 1171129Notes

Reaction equation

HRID 1171129 reaction equation
[Br:1][C:2]1[N: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[N: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 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 441182772-bromo-7-iodo-5H-pyrrolo(2,3-b)pyrazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine (258 mg, 1.3 mmol) in acetone (5 ml) was added N-iodosuccinimide (324 mg, 1.44 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 vacuum to give the title compound as a light brown solid 1H-NMR (500 MHz, d6-DMSO) δ 12.81 (s br, 1H), 8.40 (s, 1H), 8.19 (d, 3.0 Hz, 1H). MS: m/z 323.8/325.8 [MH+].

Workup

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

Sources & evidence

ORD record
ord-76a0a1e226594f67949a918c81485824
Source dataset
uspto-grants-2010_11
Patent number
US07829558B2

Reaction notes

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