849068-61-7

849068-61-7 - Names and Identifiers

Name	5-bromo-1H-pyrrolo[5,4-b]pyridine-3-carboxylic acid
Synonyms	LogP 5-Bromo-7-azaindole-3-car... 3-b]pyridine-3-carboxylic acid 5-BroMo-7-azaindole-3-carboxylic 5-Bromo-7-azaindole-3-carboxylic acid 5-Bromopyrrolo[2,3-b]pyridine-3-carboxylic Acid 5-bromo-1H-pyrrolo[5,4-b]pyridine-3-carboxylic acid 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid 5-BROMO-1H-PYRROLO[2,3-B]PYRIDINE-3-CARBOXYLIC ACID 1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-bromo- 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-bromo- acide 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylique
CAS	849068-61-7
InChI	InChI=1/C8H5BrN2O2/c9-4-1-5-6(8(12)13)3-11-7(5)10-2-4/h1-3H,(H,10,11)(H,12,13)

849068-61-7 - Physico-chemical Properties

Molecular Formula	C8H5BrN2O2
Molar Mass	241.04
Density	1.946±0.06 g/cm3(Predicted)
pKa	13.34±0.40(Predicted)
Storage Condition	2-8°C(protect from light)
Refractive Index	1.765

849068-61-7 - Risk and Safety

Risk Codes	R22 - Harmful if swallowed R36 - Irritating to the eyes
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes.
WGK Germany	3
HS Code	29339900
Hazard Class	IRRITANT

849068-61-7 - Reference Information

Use

5-bromo-1H-pyrrolo [2,3-B] pyridine -3-Formic acid is an important raw material in organic synthesis. Its derivative pyrrolo pyridine -2-formic acid amide is a glycogen phosphorylase inhibitor, it is used to prevent or treat diabetes, hypertension, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, atherosclerosis or tissue ischemia, and can be used as a cardioprotective agent.

Preparation

About 5-bromo-1H-pyrrolo [2,3-B] pyridine -3-The synthesis of formic acid can be 2-chloro -5-bromo -3-nitropyridine as raw material, 2-methyl-5-bromo-3-nitropyridine was prepared by methylation, and then 5-bromo-1H-pyrrolo [2,3-B] pyridine [2,3-B] ethyl pyridine was prepared by Reissert synthesis method through a two-step reaction, and finally the final product 5-bromo-1H-pyrrolo [2,3-B] pyridine-3-carboxylic acid was prepared by hydrolysis. In this reaction, the first step requires the use of more expensive tetra (triphenylphosphine) palladium and trimethylcycloboroxane; the second step uses ether as the solvent, which is flammable and explosive; the third step In the reaction, saturated ammonium chloride aqueous solution and iron powder are used for reduction. The post-treatment of the by-product iron mud is difficult, and the obtained product needs to be purified by column chromatography, so this method is not suitable for industrial production. In this paper, the ether is changed to methyl tert-butyl ether in the condensation reaction, which improves the safety of the reaction. Hydrogen-palladium-carbon reduction is used in the cyclization reaction, with fewer by-products, simple post-treatment, and no column chromatography purification is required, which can realize industrial production. The synthetic route is shown in Figure 1. Fig. 1 synthesis reaction formula of 5-bromo-1H-pyrrolo [2,3-B] pyridine -3-formic acid

Last Update：2024-04-09 01:59:59