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tert-Butyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate

  • CAS No. 864771-44-8

  • Cat. No. CS-0030604
  • Purity≥97%
  • MDL No.MFCD08437629

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

tert-Butyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate|CS-0030604

Structure of 864771-44-8

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General Information

  • CAS No. 864771-44-8
  • Cat. No. CS-0030604
  • Purity ≥97%
  • MDL No. MFCD08437629
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₅BN₂O₄
  • Molecular Weight 344.21
  • Synonym(s) Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indazole-1-carboxylate
  • SMILES O=C(N1N=CC2=C1C=CC(B3OC(C)(C)C(C)(C)O3)=C2)OC(C)(C)C

Description

tert-Butyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate is a bench-stable boronate ester featuring a strategically positioned indazole core. This reagent integrates seamlessly into Suzuki-Miyaura coupling protocols, enabling efficient C–C bond formation under mild conditions. The tetramethyl-1,3,2-dioxaborolane moiety enhances stability and solubility, while the tert-butyl carbamate group provides convenient protection and orthogonal deprotection options.

Application

tert-Butyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient palladium-catalyzed coupling with aryl and vinyl halides under mild conditions. The indazole core provides a rigid, bioactive scaffold commonly found in pharmaceuticals, while the tert-butyl ester offers bench stability and ease of purification. Functions as a key intermediate in the synthesis of functionalized heterocycles and drug candidates.

Synthesis

  • Route1

    References

    • GLAXOSMITHKLINE LLC; CHAUDHARI, Amita, M.; HALLMAN, Jason; LAUDEMAN, Christopher, P.; MUSSO, David, Lee; PARRISH, Cynthia, A. Patent: WO2011/66211 A1, 2011 ; Location in patent: Page/Page column 69-70 ; WO 2011/066211 A1
  • Route2

    References

    • WO2012/119046 A2, ;
  • Route3

    References

    • WO2012/119046 A2, ;

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   62.58
  • LogP   3.1187
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   1

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