4-Bromo-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoic acid 1,1-dimethylethyl ester
[CAS# 1628047-84-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 4-Bromo-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoic acid 1,1-dimethylethyl ester
• Synonyms: tert-butyl 4-bromo-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoate
• Molecular Formula: C₁₈H₁₇BrN₂O₃
• Molecular Weight: 389.24
• CAS Registry Number: 1628047-84-6
• EC Number: 942-459-8
• SMILES: CC(C)(C)OC(=O)C1=C(C=C(C=C1)Br)OC2=CN=C3C(=C2)C=CN3

Properties

• Solubility: Insoluble (3.5E^-3 g/L) (25 °C), Calc.^*
• Density: 1.445±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovery and Applications

4-Bromo-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoic acid 1,1-dimethylethyl ester, known by its chemical formula C₂₁H₂₁BrN₂O₄, is a complex organic compound with a variety of applications in chemical research and pharmaceutical development. This molecule features a benzoic acid core with a bromo substituent, an ester group, and a pyrrolo[2,3-b]pyridine moiety, which together create a structure with unique chemical properties.

The discovery of 4-bromo-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoic acid 1,1-dimethylethyl ester is rooted in the exploration of multifunctional organic compounds. The synthesis of this compound involves the introduction of a bromine atom into the benzoic acid structure, the attachment of the pyrrolo[2,3-b]pyridine group, and the esterification of the benzoic acid moiety with 1,1-dimethylethanol. This synthesis pathway highlights the complexity and precision required to create such a compound.

In terms of application, 4-bromo-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoic acid 1,1-dimethylethyl ester is primarily explored for its role in pharmaceutical research. The compound's structure suggests potential bioactivity, particularly in the development of new therapeutic agents. The presence of the pyrrolo[2,3-b]pyridine moiety is known to confer various biological activities, which makes this compound a candidate for further study in drug discovery.

The compound's unique chemical features also make it a useful intermediate in organic synthesis. Its bromo and ester groups provide sites for further chemical modifications, allowing chemists to design and synthesize a range of related molecules with tailored properties. This versatility is valuable in the creation of complex pharmaceuticals and materials.

Furthermore, the compound's role in medicinal chemistry is underscored by its potential to interact with specific biological targets. Researchers are investigating its effects on various biological pathways, aiming to identify its potential as an active ingredient in new drugs. The esterification with 1,1-dimethylethanol adds to its chemical diversity, potentially influencing its solubility and biological activity.

Overall, 4-bromo-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoic acid 1,1-dimethylethyl ester represents an important example of complex organic compounds used in pharmaceutical and chemical research. Its discovery and applications reflect its significance in the search for new therapeutic agents and its utility as a versatile building block in organic synthesis.

References

2019. Synthesis of Venetoclax. Synfacts, 15(8), 0908.
DOI: 10.1055/s-0039-1689868

2017. Venetoclax. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-22-0046