Cas no 1174038-67-5 (tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate)

Tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate is a boronic ester derivative of a pyrrolopyridine scaffold, commonly employed in Suzuki-Miyaura cross-coupling reactions for the synthesis of complex heterocyclic compounds. The tert-butyloxycarbonyl (Boc) protecting group enhances stability and facilitates selective deprotection under mild acidic conditions. The tetramethyl-1,3,2-dioxaborolane moiety offers improved solubility and handling compared to free boronic acids, while maintaining high reactivity in palladium-catalyzed transformations. This compound is particularly valuable in medicinal chemistry and materials science for constructing fused heteroaromatic systems with precise regiocontrol. Its crystalline nature and air stability further contribute to its utility in multistep synthetic workflows.
tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate structure
1174038-67-5 structure
Product Name:tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate
CAS No:1174038-67-5
MF:C18H25BN2O4
MW:344.213104963303
MDL:MFCD16660076
CID:2110432
PubChem ID:56973306
Update Time:2025-06-08

tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate
    • 1-Boc-6-Azaindole-3-boronic acid pinacol ester
    • tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-c]pyridine-1-carboxylate
    • tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate
    • (1-(TERT-BUTOXYCARBONYL)-1H-PYRROLO[2,3-C]PYRIDIN-3-YL)BORONIC ACID PINACOL ESTER
    • PB27025
    • AK173666
    • 1-Boc-1H-pyrrolo[2,3-c]pyridine-3-b
    • 1H-Pyrrolo[2,3-c]pyridine-1-carboxylic acid, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester
    • tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaboro
    • 1-N-Boc-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrrolo[2,3-c]pyridine
    • SY100289
    • TERT-BUTYL3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-C]PYRIDINE-1-CARBOXYLATE
    • CS-0048355
    • AKOS025296295
    • P11926
    • AS-51108
    • tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-c]pyridine-1-carboxylate
    • SCHEMBL13051132
    • MFCD16660076
    • 1-Boc-1H-pyrrolo[2,3-c]pyridine-3-boronic acid pinacol ester
    • Tert-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrrolo[2,3-c]pyridine-1-carboxylate
    • DA-15059
    • 1174038-67-5
    • ZWB03867
    • MDL： MFCD16660076
    • Inchi： 1S/C18H25BN2O4/c1-16(2,3)23-15(22)21-11-13(12-8-9-20-10-14(12)21)19-24-17(4,5)18(6,7)25-19/h8-11H,1-7H3
    • InChI Key： PLTWOZMQRQBRMO-UHFFFAOYSA-N
    • SMILES： O1B(C2=CN(C(=O)OC(C)(C)C)C3C=NC=CC2=3)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 344.1907374 g/mol
  • Monoisotopic Mass: 344.1907374 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 3
  • Complexity: 516
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 62.6
  • Molecular Weight: 344.2

Experimental Properties

  • Density: 1.1±0.1 g/cm3
  • Boiling Point: 470.1±48.0 °C at 760 mmHg
  • Flash Point: 238.1±29.6 °C
  • Vapor Pressure: 0.0±1.2 mmHg at 25°C

tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate Security Information

tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate Pricemore >>

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tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate Related Literature

Additional information on tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Introduction to Tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (CAS No. 1174038-67-5)

Tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate is a sophisticated organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound, identified by its CAS number 1174038-67-5, is a key intermediate in the synthesis of various biologically active molecules. Its unique structural features, particularly the presence of a tetramethyl-1,3,2-dioxaborolan-2-yl group and a pyrrolo[2,3-c]pyridine core, make it a valuable tool for researchers exploring novel drug candidates.

The tetramethyl-1,3,2-dioxaborolan-2-yl moiety is a boronic acid derivative that is widely utilized in cross-coupling reactions such as the Suzuki-Miyaura coupling. This reaction is a cornerstone in modern synthetic organic chemistry and has been instrumental in the construction of complex molecular architectures. The ability to introduce this boronic acid functionality into a heterocyclic framework like pyrrolo[2,3-c]pyridine provides chemists with a versatile platform for further functionalization and derivatization.

The significance of this compound lies in its potential applications in the development of new pharmaceuticals. Pyrrolo[2,3-c]pyridine scaffolds are known for their presence in numerous bioactive molecules, including kinase inhibitors and antiviral agents. The incorporation of a boronic acid group enhances the compound's utility in medicinal chemistry by enabling efficient modifications through cross-coupling techniques. This has led to its use in the synthesis of more complex derivatives that exhibit improved pharmacological properties.

In recent years, there has been a surge in research focused on developing novel therapeutic agents targeting cancer and infectious diseases. The structural motif of Tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate aligns well with this trend. For instance, studies have demonstrated its utility in generating derivatives that inhibit specific enzymes involved in tumor growth and viral replication. The tert-butyl ester group at the carboxyl position provides an additional handle for further chemical manipulation, allowing for the exploration of diverse pharmacophores.

The synthesis of this compound involves multi-step organic transformations that highlight the ingenuity of modern synthetic strategies. The preparation typically begins with the functionalization of a pyrrolo[2,3-c]pyridine precursor followed by the introduction of the boronic acid moiety. Advanced techniques such as palladium-catalyzed cross-coupling reactions are often employed to achieve these transformations with high efficiency and selectivity. These methods are critical for ensuring that the final product meets the stringent requirements of pharmaceutical applications.

The chemical properties of Tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate make it an attractive candidate for further investigation. Its solubility profile and stability under various conditions are essential factors that determine its suitability for different synthetic pathways. Additionally, its reactivity towards nucleophilic substitution reactions allows for the introduction of additional functional groups, expanding its synthetic utility.

In conclusion, Tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (CAS No. 1174038-67-5) represents a significant advancement in pharmaceutical chemistry. Its unique structural features and reactivity profile make it a valuable intermediate for the synthesis of biologically active molecules. As research continues to uncover new therapeutic targets and develop innovative synthetic methodologies, compounds like this one will undoubtedly play a crucial role in shaping the future of drug discovery and development.

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