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N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide

  • CAS No. 945863-21-8

  • Cat. No. CS-0091616
  • Purity≥97%
  • MDL No.MFCD08458483

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

N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide|CS-0091616

Structure of 945863-21-8

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General Information

  • CAS No. 945863-21-8
  • Cat. No. CS-0091616
  • Purity ≥97%
  • MDL No. MFCD08458483
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BN₂O₃
  • Molecular Weight 262.11
  • Synonym(s) 7 2-(N-Methylaminecarbonyl)-5-pyridineboronic acid pincol
  • SMILES O=C(C1=NC=C(B2OC(C)(C)C(C)(C)O2)C=C1)NC

Description

N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide features a boronate ester group enabling efficient Suzuki-Miyaura coupling under mild conditions. The N-methylpyridine moiety enhances solubility and metabolic stability, while the tetramethyl-substituted dioxaborolane ensures excellent shelf life and resistance to protodeboronation. This reagent streamlines late-stage functionalization in medicinal chemistry.

Application

N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide serves as a versatile boronate building block for Suzuki-Miyaura coupling reactions. The picolinamide moiety provides directional coordination and enhanced stability, while the tetramethylboronate group enables efficient cross-coupling under mild conditions. This compound exhibits excellent bench stability, tolerates common functional groups, and facilitates the construction of biologically relevant heterocyclic scaffolds in medicinal chemistry and materials synthesis.

Synthesis

  • Route1

    References

    • WO2010/8847 A2, ; Page/Page column 125-126 ;

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

Quality Control

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Computational Chemistry Data

  • TPSA   60.45
  • LogP   0.7404
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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