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

Name: 5-(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. 754214-56-7
Cat. No. CS-B0499
Purity≥97%
MDL No.MFCD08060937

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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine|CS-B0499

Structure of 754214-56-7

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General Information

CAS No. 754214-56-7
Cat. No. CS-B0499
Purity ≥97%
MDL No. MFCD08060937
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₇BN₂O₂
Molecular Weight 244.10
Synonym(s) 7-Azaindole-5-boronic acid pinacol ester
SMILES CC1(C)OB(C2=CN=C3NC=CC3=C2)OC(C)1C

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine is a boronate ester-functionalized heterocycle featuring a pyrrolo[2,3-b]pyridine core. This stable, bench-ready reagent integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. The tetramethyl dioxaborolane moiety enhances solubility and reaction kinetics while maintaining high functional group tolerance.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. Its stability under ambient conditions and compatibility with diverse functional groups enable efficient construction of biaryl scaffolds in medicinal chemistry and materials science. The tetramethylborolane moiety facilitates reliable Suzuki-Miyaura coupling, offering high chemoselectivity and ease of purification.

Synthesis

Route1
- In-stock
  
  73183-34-3
- In-stock
  
  183208-35-7
- ~94%
- In-stock
  
  754214-56-7
References
- US2008/153860 A1, ; Page/Page column 24 ;
Route2
- In-stock
  
  271-63-6
- In-stock
  
  73183-34-3
- ~42%
- In-stock
  
  754214-56-7
References
- WO2006/63167 A1, ; Page/Page column 67-68 ; WO 2006/063167 A1

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+H312+H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-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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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

CAS No. 754214-56-7

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