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tert-Butyl 3-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate

  • CAS No. 877399-35-4

  • Cat. No. CS-0048341
  • Purity≥98%
  • MDL No.None

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

tert-Butyl 3-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate|CS-0048341

Structure of 877399-35-4

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General Information

  • CAS No. 877399-35-4
  • Cat. No. CS-0048341
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₈BN₃O₄
  • Molecular Weight 349.23
  • Synonym(s) Tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrazol-1-YL)azetidine-1-carboxylate
  • SMILES CC(C)(C)OC(=O)N1CC(C1)N1C=C(C=N1)B1OC(C)(C)C(C)(C)O1

Description

tert-Butyl 3-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate features a boronate ester linked to a pyrazole-substituted azetidine scaffold, enabling efficient cross-coupling reactions. This bench-stable reagent integrates readily into diverse synthetic sequences, delivering complex heterocyclic architectures with high functional group tolerance and predictable regiochemistry under standard conditions.

Application

tert-Butyl 3-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate serves as a versatile boron-containing building block for Suzuki-Miyaura coupling reactions. The pyrazole moiety provides robust stability and orthogonal reactivity, while the azetidine scaffold offers a constrained, bioactive core amenable to further derivatization. Bench-stable and compatible with diverse reaction conditions, it facilitates efficient construction of complex heterocyclic architectures in medicinal chemistry and API development workflows.

Synthesis

  • Route1

    References

    • Cui, J. Jean; Tran-Dube, Michelle; Shen, Hong; Nambu, Mitchell; Kung, Pei-Pei; Pairish, Mason; Jia, Lei; Meng, Jerry; Funk, Lee; Botrous, Iriny; McTigue, Michele; Grodsky, Neil; Ryan, Kevin; Padrique, Ellen; Alton, Gordon; Timofeevski, Sergei; Yamazaki, Shinji; Li, Qiuhua; Zou, Helen; Christensen, James; Mroczkowski, Barbara; Bender, Steve; Kania, Robert S.; Edwards, Martin P. Journal of Medicinal Chemistry, 2011 , vol. 54, # 18 p. 6342 - 6363
  • Route2

    References

    • NOVARTIS AG Patent: WO2008/148867 A2, 2008 ; Location in patent: Page/Page column 59-60 ; WO 2008/148867 A2
  • Route3

    References

    • Cui, J. Jean; Tran-Dube, Michelle; Shen, Hong; Nambu, Mitchell; Kung, Pei-Pei; Pairish, Mason; Jia, Lei; Meng, Jerry; Funk, Lee; Botrous, Iriny; McTigue, Michele; Grodsky, Neil; Ryan, Kevin; Padrique, Ellen; Alton, Gordon; Timofeevski, Sergei; Yamazaki, Shinji; Li, Qiuhua; Zou, Helen; Christensen, James; Mroczkowski, Barbara; Bender, Steve; Kania, Robert S.; Edwards, Martin P. Journal of Medicinal Chemistry, 2011 , vol. 54, # 18 p. 6342 - 6363

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   65.82
  • LogP   1.9741
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   2

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