N-Iodosuccinimide → 6-Bromo-3-iodo-8-(methylthio)imidazo[1,2-a]pyrazine

HRID 925587Notes

Reaction equation

HRID 925587 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([S:11][CH3:12])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.C1C(=O)N([I:20])C(=O)C1>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([S:11][CH3:12])[C:5]2[N:6]([C:8]([I:20])=[CH:9][N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 532498696-Bromo-8-(methylthio)imidazo[1,2-A]pyrazine

Product 1

HCID 575996096-Bromo-3-iodo-8-(methylthio)imidazo[1,2-a]pyrazineYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 6-bromo-8-methylsulfanyl-imidazo[1,2-a]pyrazine (210.0 g, 860.3 mmol) in DMF (4200 mL) was added NIS (212.9 g, 946.3 mmol, 1.1 eq) in one portion at rt. After 18 h stirring at 60° C. the dark solution was evaporated and the brown residue was dissolved in DCM (7 L), washed with water (2×5 L) and sole (2×5 L) and dried over sodium sulphate. Crystallization by careful removal of solvent yielded 255 g (80.1%) 6-bromo-3-iodo-8-methylsulfanyl-imidazo[1,2-a]pyrazine: 1H-NMR (300 MHz, d6-DMSO): δ=8.24 (1H, s), 7.79 (1H, s), 2.46 (3H, s) ppm.

Workup

  1. customwas evaporated
  2. dissolutionthe brown residue was dissolved in DCM (7 L)
  3. washwashed with water (2×5 L) and sole (2×5 L)
  4. dry with materialdried over sodium sulphate
  5. customCrystallization
  6. customby careful removal of solvent

Sources & evidence

ORD record
ord-df367ee5962c4b22bdc449d82047e88c
Source dataset
uspto-grants-2016_03
Patent number
US09284317B2

Reaction notes

Loading…