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Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate

  • CAS No. 736990-02-6

  • Cat. No. CS-0041032
  • Purity≥97%
  • MDL No.MFCD11894323

*For research and further manufacturing use only, not for direct human use.

Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate|CS-0041032

Structure of 736990-02-6

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General Information

  • CAS No. 736990-02-6
  • Cat. No. CS-0041032
  • Purity ≥97%
  • MDL No. MFCD11894323
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₂BNO₄
  • Molecular Weight None
  • Synonym(s) 2-Ethoxycarbonylindole-5-boronic acid pinacol ester
  • SMILES O=C(C(N1)=CC2=C1C=CC(B3OC(C)(C)C(C)(C)O3)=C2)OCC

Description

Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate integrates a boronate ester group with a functionalized indole scaffold, enabling efficient Suzuki-Miyaura coupling under mild conditions. This bench-stable reagent features enhanced solubility in common organic solvents and tolerates diverse reaction environments, facilitating rapid access to biologically relevant indole derivatives.

Application

Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. The tetramethylboronate group enables efficient Suzuki-Miyaura coupling under mild conditions, while the indole core and ester functionality offer orthogonal reactivity for downstream transformations. Bench-stable and readily purified by flash chromatography, it facilitates rapid access to substituted indole scaffolds in medicinal chemistry and materials synthesis.

Synthesis

  • Route1

    References

    • F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BAUMANN, Karlheinz; FLOHR, Alexander; JOLIDON, Synese; KNUST, Henner; LUEBBERS, Thomas; NETTEKOVEN, Matthias Patent: WO2014/60386 A1, 2014 ; Location in patent: Page/Page column 44 ;
  • Route2

    References

    • F. Hoffmann-La Roche AG; The designation of the inventor has not yet been filed Patent: EP2722329 A1, 2014 ;
  • Route3

    References

    • BIOLIPOX AB Patent: WO2005/123674 A1, 2005 ; Location in patent: Page/Page column 58 ; WO 2005/123674 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   60.55
  • LogP   2.6438
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   3

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