1H-Pyrrolo[2,3-b]pyridine, 5-fluoro-

1H-Pyrrolo[2,3-b]pyridine, 5-fluoro- - Names and Identifiers

Name	5-FLUORO-1H-PYRROLO[2,3-B]PYRIDINE
Synonyms	SW-10 SWF-10 EOS-60587 5-FLUORO-7-AZAINDOLE 5-Fluoro-7-Azaindole 5-Fluoro-1H-pyrrolo[2,3-b]pyridin 5-FLUORO-1H-PYRROLO[2,3-B]PYRIDINE 1H-Pyrrolo[2,3-b]pyridine, 5-fluoro- 5-Fluoro-7-azaindole (5-Fluoro-1H-pyrrolo[2,3-b]pyridine)
CAS	866319-00-8
InChI	InChI=1/C7H5FN2/c8-6-3-5-1-2-9-7(5)10-4-6/h1-4H,(H,9,10)
InChIKey	BALBNSFYMXBWNM-UHFFFAOYSA-N

1H-Pyrrolo[2,3-b]pyridine, 5-fluoro- - Physico-chemical Properties

Molecular Formula	C7H5FN2
Molar Mass	136.13
Density	1.35
Melting Point	112-113°C
pKa	13.04±0.40(Predicted)
Storage Condition	Sealed in dry,Room Temperature
Refractive Index	1.658
Use	This product is for scientific research only and shall not be used for other purposes.

1H-Pyrrolo[2,3-b]pyridine, 5-fluoro- - Risk and Safety

Risk Codes	R22 - Harmful if swallowed R41 - Risk of serious damage to eyes
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection.
WGK Germany	3
HS Code	29339900
Hazard Class	IRRITANT

1H-Pyrrolo[2,3-b]pyridine, 5-fluoro- - Reference Information

Application prospect

5-fluoro-1h-pyrrolo [2,3-B] pyridine is an important pharmaceutical intermediate. The pyrrolo pyridine skeleton can be divided into pyrrolo [3,2-b] pyridine, pyrrolo [3,4-b] pyridine, pyrrolo [2,3-b] pyridine and other six different structures. Pyrrole and pyridine compounds are cyclized to form heterocyclic compounds with pyrrolopyridine or structural characteristics, which show potential biological activities, many new active intermediates, in turn, have become important raw materials in drug synthesis, designing and innovating drugs with excellent biological activity and little toxic and side effects, research topics that are always of common concern and great interest to developers of organic synthesis and pharmaceutical research. Such derivatives are present in alkaloids such as ASP3627, mappicin, Vemurafenib and the like, and can be used as LRRK2 inhibitors, MPS1 inhibitors, JAK1 inhibitors, Met kinase inhibitors and the like.

preparation

5-fluoro-1h-pyrrolo [2,3-B] pyridine can be used for the synthesis of novel fluoroquinolone drugs. At present, the market demand is large and the price is relatively high. Scientists from various countries have done a lot of research on its synthesis. Patent DE4208792 reported the structure of this bicyclic parent structure of the method, 2, 3-dicarboxylic acid pyridine as raw material, esterification, reduction, chlorination, and then with sodium hydride and p-toluenesulfonamide for cyclization, for the preparation of pyrrolo-pyridine ring compounds, intramolecular cyclization may also occur to prepare 5-fluoro-1h-pyrrolo [2,3-B] pyridine, and the synthesis reaction scheme is shown below. Fig.1 reaction formula for the synthesis of 5-fluoro-1h-pyrrolo [2,3-B] pyridine 3-acetyl-5-fluoropyridin-2-amine is dissolved in anhydrous methanol, in addition, the catalytic amount of glacial acetic acid was added, and 70.0 mg (1.10 mmol) of sodium cyanoborohydride was weighed in N 2 gas, mixed well, stirred and heated to 60 ℃ in the flask, and the progress of the reaction was monitored by thin layer chromatography, the reaction was stopped until no reactant was seen, and the product was detected by TLC (methanol developing solvent) with Rf = 0.57. The reaction mixture was dissolved in dichloromethane and washed twice with water. The organic phase was dried over anhydrous sodium sulfate and the mixture was separated by silica gel column chromatography, the product was dried in vacuo to give 5-fluoro-1h-pyrrolo [2,3-B] pyridine.

Last Update：2024-04-09 21:04:16