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

Name: 1-(Benzenesulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine
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CAS No. 1174038-65-3
Cat. No. CS-0052846
Purity≥97%
MDL No.None

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1-(Benzenesulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine|CS-0052846

Structure of 1174038-65-3

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General Information

CAS No. 1174038-65-3
Cat. No. CS-0052846
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₉H₂₁BN₂O₄S
Molecular Weight 384.26
Synonym(s) 1-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine
SMILES CC1(C)OB(OC1(C)C)C1=CN(C2=CN=CC=C12)S(=O)(=O)C1=CC=CC=C1

Description

1-(Benzenesulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine integrates a boronate handle with a bench-stable, electron-deficient pyrrolopyridine core. This reagent enables direct Suzuki-Miyaura coupling under mild conditions, facilitating efficient access to substituted heteroaryl scaffolds in medicinal chemistry and materials synthesis.

Application

1-(Benzenesulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. The pyrrolo[2,3-c]pyridine core provides a rigid, electron-deficient heteroaromatic scaffold with established utility in medicinal chemistry. The benzenesulfonyl group enhances solubility and stability, while the diborane moiety enables efficient Suzuki-Miyaura coupling under mild conditions, facilitating rapid access to functionalized analogs.

Synthesis

Route1
- 1174038-64-2
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  1174038-65-3
References
- Merck Patent Gesellschaft Mit Beschrankter Haftung Patent: US2010/292262 A1, 2010 ; Location in patent: Page/Page column 13-14 ;

Safety Information

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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 70.42
LogP 2.5725
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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1-(Benzenesulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine

CAS No. 1174038-65-3

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