| Identification | Back Directory | [Name]
1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile, 4-chloro- | [CAS]
920966-02-5 | [Synonyms]
3-b]pyridine-5-carbonitrile
4-Chloro-5-cyano-7-azaind...
4-Chloro-5-cyano-7-azaindole
6-Fluoro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde
4-Chloro-1H-Pyrrollo[2,3-b]pyridine-5-carbonitrile
1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile, 4-chloro-
1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile, 4-chloro- ISO 9001：2015 REACH | [Molecular Formula]
C8H4ClN3 | [MDL Number]
MFCD09965877 | [MOL File]
920966-02-5.mol | [Molecular Weight]
177.59 |
| Questions And Answer | Back Directory | [Synthesis]
There are many reported methods for constructing the bicyclic parent structure of pyrrolo[2,3-B]pyridine. Using 2,3-dicarboxylic acid pyridine as a raw material, pyrrolopyridine cyclic compounds are prepared by esterification, reduction, chlorination, and then cyclization with sodium hydride and p-toluenesulfonamide. Intramolecular cyclization can also be performed to prepare 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile. The synthetic reaction formula is shown in the figure below. 
Figure 1 Synthesis reaction formula of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile Experimental procedure: 3-acetylen-4-chloropyridine-2-amine-5-carboxynitrile was dissolved in anhydrous methanol, and a catalytic amount of glacial acetic acid was added. 70.0 mg (1.10 mmol) of sodium cyanoborohydride was weighed in N2 gas. The mixture was stirred and heated to 60°C in a flask. The reaction progress was monitored by thin-layer chromatography until no reactants were observed. The reaction was stopped. TLC detection (methanol eluent) showed that the product Rf = 0.57. The reaction mixture was evaporated to dryness, dissolved in dichloromethane, washed twice with purified water, and the organic phase was dried over anhydrous sodium sulfate. The mixture was then separated by silica gel column chromatography, and the product was dried under vacuum to give 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile. | [Uses]
4-Chloro-1H-pyrrolo[2,3-B]pyridine-5-carboxynitrile can be used in biological research. The pyrrolopyridine skeleton can be classified into six different structures according to the different combinations of pyrrole and pyridine: pyrrolo[3,2-b]pyridine, pyrrolo[3,4-b]pyridine, and pyrrolo[2,3-b]pyridine. Cyclization of pyrrole and pyridine compounds forms heterocyclic compounds with pyrrolopyridine or similar structural characteristics, all exhibiting potential biological activity. Many new active intermediates subsequently become important raw materials in drug synthesis. Designing and innovatively synthesizing drugs with excellent biological activity and low toxicity is always a research topic of common concern and great interest to organic synthetic and drug research developers. These derivatives exist in alkaloids such as ASP3627, Mappicine, and Vemurafenib, and can be used as LRRK2 inhibitors, MPS1 inhibitors, JAK1 inhibitors, and Met kinase inhibitors. |
| Chemical Properties | Back Directory | [density ]
1.50 | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
solid | [pka]
11.60±0.40(Predicted) | [Appearance]
White to light brown Solid | [InChI]
InChI=1S/C8H4ClN3/c9-7-5(3-10)4-12-8-6(7)1-2-11-8/h1-2,4H,(H,11,12) | [InChIKey]
ULYGKPKPBWOTFQ-UHFFFAOYSA-N | [SMILES]
C12NC=CC1=C(Cl)C(C#N)=CN=2 |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301 | [Precautionary statements ]
P301+P310 | [Hazard Codes ]
T | [Risk Statements ]
25 | [Safety Statements ]
45 | [RIDADR ]
UN 2811 6.1 / PGIII | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral |
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