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

Name: 5-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1h-pyrrolo[2,3-b]pyridine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 866546-11-4
Cat. No. CS-0005128
Purity≥97%
MDL No.MFCD16039195

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5-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1h-pyrrolo[2,3-b]pyridine|CS-0005128

Structure of 866546-11-4

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General Information

CAS No. 866546-11-4
Cat. No. CS-0005128
Purity ≥97%
MDL No. MFCD16039195
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₂BClN₂O₄S
Molecular Weight 432.73
Synonym(s) 1H-Pyrrolo[2,3-b]pyridine, 5-chloro-1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)
SMILES O=S(N1C(C(C(B(OC(C)2C)OC2(C)C)=C1)=C3)=NC=C3Cl)(C(C=C4)=CC=C4C)=O

Description

5-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1h-pyrrolo[2,3-b]pyridine features a boronate ester group enabling efficient Suzuki-Miyaura coupling. The tosyl moiety enhances solubility and stability, while the chloropyrrolopyridine core provides a rigid scaffold for diversification in medicinal chemistry and materials synthesis under standard conditions.

Application

5-Chloro-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 palladium-catalyzed cross-coupling reactions. The tosyl group enhances stability and modulates reactivity, while the pinacol boronate enables efficient Suzuki-Miyaura coupling under mild conditions. This scaffold is well-suited for constructing complex heterocyclic architectures in medicinal chemistry and materials science.

Synthesis

Route1
- 866546-10-3
- In-stock
  
  73183-34-3
- ~50%
- In-stock
  
  866546-11-4
References
- VERTEX PHARMACEUTICALS INCORPORATED? Patent: WO2005/95400 A1, 2005 ; Location in patent: Page/Page column 345; 348 ; WO 2005/095400 A1
Route2
- In-stock
  
  1072-98-6
- ~%
- In-stock
  
  866546-11-4
References
- MERCK SHARP and DOHME CORP.; CASH, Brandon; FISCHER, Christian; GARCIA, Yudith; JUNG, Joon; KATZ, Jason; KIM, June; RIVKIN, Alexey; SCHELL, Adam; SIU, Tony; WITTER, David; ZHOU, Hua Patent: WO2011/137022 A1, 2011 ;
Route3
- In-stock
  
  211308-81-5
- ~%
- In-stock
  
  866546-11-4
References
- MERCK SHARP and DOHME CORP.; CASH, Brandon; FISCHER, Christian; GARCIA, Yudith; JUNG, Joon; KATZ, Jason; KIM, June; RIVKIN, Alexey; SCHELL, Adam; SIU, Tony; WITTER, David; ZHOU, Hua Patent: WO2011/137022 A1, 2011 ;

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-P330-P362-P405-P501

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Computational Chemistry Data

TPSA 70.42
LogP 3.53432
H_Acceptors 6
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Chloride

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

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

CAS No. 866546-11-4

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