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

Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine
Brand: ChemScene
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CAS No. 942919-26-8
Cat. No. CS-B0489
Purity≥98%
MDL No.MFCD11616360

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine|CS-B0489

Structure of 942919-26-8

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General Information

CAS No. 942919-26-8
Cat. No. CS-B0489
Purity ≥98%
MDL No. MFCD11616360
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₇BN₂O₂
Molecular Weight 244.10
Synonym(s) 7-azaindole-4-boronic acid pinacol ester
SMILES CC1(C)OB(C2=C3C(NC=C3)=NC=C2)OC(C)1C

Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine features a boronate ester group flanked by a tetramethyl-substituted dioxaborolane ring, enabling stable coupling in Suzuki-Miyaura reactions. The electron-deficient pyrrolo[2,3-b]pyridine core integrates readily into heterocyclic scaffolds under standard conditions. This bench-stable reagent streamlines access to complex nitrogen-rich architectures.

Application

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine serves as a versatile boronate building block in palladium-catalyzed cross-coupling reactions. Its stability under ambient conditions and compatibility with diverse functional groups enable efficient construction of biaryl architectures. The tetramethyl-substituted dioxaborolane moiety facilitates reliable coupling with aryl halides and pseudohalides, making it well-suited for synthesizing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  73183-34-3
- In-stock
  
  55052-28-3
- ~93%
- In-stock
  
  942919-26-8
References
- S BIO PTE LTD Patent: WO2009/93981 A1, 2009 ; Location in patent: Page/Page column 106 ; WO 2009/093981 A1
Route2
- In-stock
  
  73183-34-3
- In-stock
  
  348640-06-2
- ~62%
- In-stock
  
  942919-26-8
References
- Adams, Nicholas D.; Adams, Jerry L.; Burgess, Joelle L.; Chaudhari, Amita M.; Copeland, Robert A.; Donatelli, Carla A.; Drewry, David H.; Fisher, Kelly E.; Hamajima, Toshihiro; Hardwicke, Mary Ann; Huffman, William F.; Koretke-Brown, Kristin K.; Lai, Zhihong V.; McDonald, Octerloney B.; Nakamura, Hiroko; Newlander, Ken A.; Oleykowski, Catherine A.; Parrish, Cynthia A.; Patrick, Denis R.; Plant, Ramona; Sarpong, Martha A.; Sasaki, Kosuke; Schmidt, Stanley J.; Silva, Domingos J.; Sutton, David; Tang, Jun; Thompson, Christine S.; Tummino, Peter J.; Wang, Jamin C.; Xiang, Hong; Yang, Jingsong; Dhanak, Dashyant Journal of Medicinal Chemistry, 2010 , vol. 53, # 10 p. 3973 - 4001

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 47.14
LogP 1.8621
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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

CAS No. 942919-26-8

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