3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Name: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 866545-91-7
Cat. No. CS-0004209
Purity≥97%
MDL No.MFCD11616456

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3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine|CS-0004209

Structure of 866545-91-7

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General Information

CAS No. 866545-91-7
Cat. No. CS-0004209
Purity ≥97%
MDL No. MFCD11616456
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₃BN₂O₄S
Molecular Weight 398.28
Synonym(s) 1-[(4-Methylbenzene)sulfonyl]-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester
SMILES O=S(N(C1=NC=CC=C12)C=C2B(OC(C)3C)OC3(C)C)(C(C=C4)=CC=C4C)=O

Description

This boronate-functionalized pyrrolopyridine integrates readily into Suzuki-Miyaura coupling reactions, offering high stability and compatibility with diverse reaction conditions. The tosyl group enhances solubility and directs regioselective transformation, enabling efficient synthesis of complex heterocyclic architectures under standard bench protocols.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tosyl group enhances stability and modulates reactivity, while the tetramethylborolane moiety enables efficient coupling under mild conditions. This compound exhibits excellent bench stability, facilitates purification by standard chromatography, and functions reliably in the construction of complex heterocyclic scaffolds relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  73183-34-3
- 226085-18-3
- ~96%
- In-stock
  
  866545-91-7
References
- VERTEX PHARMACEUTICALS INCORPORATED? Patent: WO2005/95400 A1, 2005 ; Location in patent: Page/Page column 326; 327 ; WO 2005/095400 A1
Route2
- In-stock
  
  76-09-5
- 882562-39-2
- ~81%
- In-stock
  
  866545-91-7
References
- VERTEX PHARMACEUTICALS INCORPORATED; TAYLOR, Lori, Kell; SEWELL, Kathryn, Lea; HOOCK, Thomas, Carl Patent: WO2014/74471 A1, 2014 ; Location in patent: Paragraph 0278-0280 ;
Route3
- 226085-18-3
- ~%
- In-stock
  
  866545-91-7
References
- WO2013/6634 A2, ;

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 70.42
LogP 2.88092
H_Acceptors 6
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

CAS No. 866545-91-7

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