2-bromo-7-iodo-5H-pyrrolo[3,2-b]pyrazine

2-bromo-7-iodo-5H-pyrrolo[3,2-b]pyrazine - Names and Identifiers

Name	5H-Pyrrolo[2,3-b]pyrazine,2-bromo-7-iodo-
Synonyms	2-broMo-7-iodo-5H-pyrrolo[2 5-Bromo-3-iodo-4,7-diazaindole 2-Bromo-7-iodo-5H-pyrrolo[2,3-b]pyrazine 2-BROMO-7-IODO-5H-PYRROLO[2,3-B]PYRAZINE 2-Bromo-7-iodo-5H-pyrrolo[3,2-b]pyrazine 2-bromo-7-iodo-4H-pyrrolo[2,3-b]pyrazine 5H-Pyrrolo[2,3-b]pyrazine,2-bromo-7-iodo- 4H-Pyrrolo[2,3-b]pyrazine,2-bromo-7-iodo- (9CI) 2-bromo-7-iodo-5H-pyrrolo[2,3-b]pyrazine 2-bromo-7-iodo-5H-pyrrolo[3,2-b]pyrazine
CAS	875781-44-5
InChI	InChI=1S/C6H3BrIN3/c7-4-2-10-6-5(11-4)3(8)1-9-6/h1-2H,(H,9,10)

2-bromo-7-iodo-5H-pyrrolo[3,2-b]pyrazine - Physico-chemical Properties

Molecular Formula	C6H3BrIN3
Molar Mass	323.92
Density	2.78
Boling Point	311℃
Flash Point	142℃
pKa	9.08±0.50(Predicted)
Storage Condition	under inert gas (nitrogen or Argon) at 2–8 °C

2-bromo-7-iodo-5H-pyrrolo[3,2-b]pyrazine - Reference Information

use

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

There are two synthetic strategies for preparing

pyrrolo pyrazine bicyclic compounds and their analogs. Using the pyrazine ring as the raw material, the pyrrolo-pyrazine bicyclic compound is obtained through the nucleophilic substitution, hydroxyl chloride, and ring closure of the amino alcohol; the pyrrole or imidazole ring is used as the raw material, and the key is formed by cyclizing with the ketone group Intermediate, then react with ammonium acetate, and finally use the conditions of phosphorus oxychloride reflux to obtain pyrrolo-pyrazine compounds. Preparation of 2-bromo-7-iodo-5H-pyrrolo [2,3-B] pyrazine With pyrazin-2-bromo-7-iodo-5-amine and ethanol as starting materials, it is prepared by cyclization and dehydration reaction. It can also be prepared from 2-bromo-5H-pyrrolo [2,3-B] pyrazine by iodine. The synthesis reaction formula is as follows: Figure 1 2-Bromo -7-Iodine-5H-pyrrolo [2,3-B] Pyrazine synthesis reaction formula Add N,N-dimethylformamide into a 250 mL three-mouth bottle, start the stirring device, add pyrazine -2-bromo -7-iodine -5-amine and absolute ethanol, under the protection of nitrogen, raise the temperature to 50 ℃ in a heating reactor, and stir for 5 hours, TLC detection of reaction progress. After the reaction, stop heating and place at room temperature. The reaction solution is slowly poured into ice water, extracted with ethyl acetate (50 mL × 3), combined with organic phases, dried with anhydrous sodium sulfate, filtered, concentrated filtrate, and purified by column chromatography to obtain colorless oil. Add the above oil and absolute ethanol into a 250 mL three-mouth bottle, start the stirring device, add concentrated sulfuric acid dropwise, raise the temperature to 90 ℃ in a heating reactor, stir for 4 hours, and detect the reaction progress by thin layer chromatography. After the reaction, stop heating and place at room temperature. The reaction solution was slowly poured into ice water, extracted with ethyl acetate (50 mL × 3), combined with organic phases, dried with anhydrous sodium sulfate, filtered, and concentrated to obtain pure 2-bromo-7-iodo-5H-pyrrolo [2,3-B] pyrazine.

Last Update：2024-04-09 21:04:16