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N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide

  • CAS No. 1201645-46-6

  • Cat. No. CS-0036586
  • Purity≥97%
  • MDL No.MFCD11878288

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

N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide|CS-0036586

Structure of 1201645-46-6

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General Information

  • CAS No. 1201645-46-6
  • Cat. No. CS-0036586
  • Purity ≥97%
  • MDL No. MFCD11878288
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BN₂O₃
  • Molecular Weight None
  • Synonym(s) 5-N-Acetyl-amino-pyridin-3-ylboronic acid pinacol ester
  • SMILES CC(=NC1=CN=CC(=C1)B2OC(C)(C)C(C)(C)O2)O

Description

N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide features a pyridine-linked boronate ester enabling robust Suzuki-Miyaura coupling under mild conditions. The tetramethyl-substituted dioxaborolane imparts enhanced stability and moisture tolerance, while the acetamide group provides solubility and compatibility in diverse reaction media. This reagent integrates seamlessly into complex molecule assembly workflows.

Application

N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pyridine core enables transition-metal-catalyzed coupling with aryl, heteroaryl, and vinyl halides under mild conditions. The acetamide group provides enhanced solubility and stability, while the tetramethyl-substituted dioxaborolane offers excellent bench stability and functional group tolerance. This reagent facilitates efficient construction of biaryl and heterobiaryl scaffolds in medicinal chemistry and materials synthesis workflows.

Synthesis

  • Route1

    References

    • WO2009/155527 A2, ; Page/Page column 254 ; WO 2009/155527 A2

Safety Information

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Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

  • TPSA   63.94
  • LogP   1.9887
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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