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1H-Indazole-1-carboxylic acid, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester

  • CAS No. 890839-29-9

  • Cat. No. CS-0030617
  • Purity≥97%
  • MDL No.MFCD13183032

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

1H-Indazole-1-carboxylic acid, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester|CS-0030617

Structure of 890839-29-9

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General Information

  • CAS No. 890839-29-9
  • Cat. No. CS-0030617
  • Purity ≥97%
  • MDL No. MFCD13183032
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₅BN₂O₄
  • Molecular Weight 344.21
  • Synonym(s) 1H-Indazole-1-carboxylic acid, 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-diMethylethyl ester
  • SMILES O=C(N1N=CC2=C1C=C(B3OC(C)(C)C(C)(C)O3)C=C2)OC(C)(C)C

Description

tert-Butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate delivers a stable, bench-ready boronate handle for Suzuki-Miyaura cross-coupling. The tetramethyl-substituted dioxaborolane enhances reactivity and shelf stability, while the indazole scaffold provides a rigid, electron-deficient platform ideal for medicinal chemistry applications.

Application

tert-Butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The indazole core provides a privileged scaffold in medicinal chemistry, while the pinacol boronate ester enables reliable C–C bond formation under mild conditions. Functional group tolerance and ease of purification support its use in diverse synthetic sequences, including the construction of complex heterocyclic systems and API intermediates.

Synthesis

  • Route1

    References

    • GLAXOSMITHKLINE LLC; DOCK, Steven, Thomas; MCSHERRY, Allison, K.; MOORE, Michael, Lee; RIDGERS, Lance, Howard; PARRISH, Cynthia, Ann Patent: WO2013/28445 A1, 2013 ; Location in patent: Page/Page column 55 ;
  • Route2

    References

    • WO2012/37298 A1, ; WO 2012/037298 A1
  • Route3

    References

    • WO2013/28445 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 : H319-H413
Precautionary Statements : P264-P273-P280-P501

Quality Control

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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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