2-BROMO-7-IODO-5H-PYRROLO[2,3-B]PYRAZINE Chemical Properties

Boiling point:

311℃

Density 

2.78

Flash point:

142℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

9.08±0.50(Predicted)

Appearance

Light yellow to yellow Solid

2-BROMO-7-IODO-5H-PYRROLO[2,3-B]PYRAZINE Usage And Synthesis

Uses

2-Bromo-7-iodo-5H-pyrrolo[2,3-B]pyrazine is a common pyrrolo[2,3-B]pyrazine bicyclic compound, widely used in the preparation of pharmaceutical and chemical intermediates.

Synthesis

Step 1. Synthesis of 2-bromo-7-iodo-5H-pyrrolo[2,3-b]pyrazine. To a solution of N,N-dimethylformamide (DMF, 160 mL) of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (8 g, 40.4 mmol) was added N-iodosuccinimide (NIS, 11.8 g, 3.6 mmol) and the reaction mixture was stirred for 1 hour at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio of petroleum ether: ethyl acetate = 2:1) to confirm the completion of the reaction. The reaction mixture was diluted with water (500 mL) and extracted with ethyl acetate (EtOAc, 300 mL x 3). The organic phases were combined, washed with saturated saline and dried over anhydrous sodium sulfate (Na2SO4). After filtration, the solvent was removed by concentration under reduced pressure to afford 2-bromo-7-iodo-5H-pyrrolo[2,3-b]pyrazine (26.1 g, 100% yield) as a brown solid (containing a small amount of DMF).

References

[1] Patent: US2015/158864, 2015, A1. Location in patent: Paragraph 0645
[2] Patent: WO2010/15803, 2010, A1. Location in patent: Page/Page column 43
[3] Patent: WO2010/68483, 2010, A2. Location in patent: Page/Page column 68
[4] Patent: WO2011/149950, 2011, A2. Location in patent: Page/Page column 65; 67
[5] Patent: WO2014/85795, 2014, A1. Location in patent: Paragraph 0283

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