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

  • CAS No. 777061-36-6

  • Cat. No. CS-0091567
  • Purity≥96%
  • MDL No.MFCD05663895

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

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate|CS-0091567

Structure of 777061-36-6

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General Information

  • CAS No. 777061-36-6
  • Cat. No. CS-0091567
  • Purity ≥96%
  • MDL No. MFCD05663895
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₉H₂₆BNO₄
  • Molecular Weight 343.23
  • Synonym(s) TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLE-1-CARBOXYLATE
  • SMILES O=C(N1C=CC2=C1C=CC(B3OC(C)(C)C(C)(C)O3)=C2)OC(C)(C)C

Description

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate delivers a boronate-functionalized indole scaffold with enhanced stability and moisture tolerance. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura coupling protocols, enabling efficient C–C bond formation under standard conditions. The tetramethyl dioxaborolane moiety ensures high reactivity and compatibility with diverse reaction matrices.

Application

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The indole core is protected as a tert-butyl carbamate, offering excellent functional group tolerance and compatibility with diverse reaction conditions. Its tetramethyl-substituted dioxaborolane moiety enables reliable coupling with aryl and heteroaryl halides, facilitating the construction of biologically relevant indole scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • MERCK SHARP and DOHME CORP.; MCCOMAS, Casey Cameron; LIVERTON, Nigel J.; HABERMANN, Joerg; KOCH, Uwe; NARJES, Frank; LI, Peng; PENG, Xuanjia; SOLL, Richard; WU, Hao; PALANI, Anandan; DAI, Xing; LIU, Hong; HE, Shuwen; DANG, Qung Patent: WO2013/34048 A1, 2013 ; Location in patent: Page/Page column 90 ;
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 69, # 20 p. 6812 - 6820
  • Route3

    References

    • Craig, Sandra; Gao, Lei; Lee, Irene; Gray, Thomas; Berdis, Anthony J. Journal of Medicinal Chemistry, 2012 , vol. 55, # 5 p. 2437 - 2451

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H413
Precautionary Statements : P264-P273-P280-P302+P352-P362+P364-P501

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Computational Chemistry Data

  • TPSA   49.69
  • LogP   3.7237
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   1

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