4-Chloro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridin-5-ol

Name: 4-Chloro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridin-5-ol
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 685513-98-8
Cat. No. CS-0004166
Purity≥98%
MDL No.MFCD11616410

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4-Chloro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridin-5-ol|CS-0004166

Structure of 685513-98-8

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General Information

CAS No. 685513-98-8
Cat. No. CS-0004166
Purity ≥98%
MDL No. MFCD11616410
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₂₅ClN₂OSi
Molecular Weight 324.92
Synonym(s) 4-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol
SMILES ClC1=C2C(N([Si](C(C)C)(C(C)C)C(C)C)C=C2)=NC=C1O

Description

4-Chloro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridin-5-ol features a sterically shielded silyl group that enhances stability and solubility in organic media. This bench-stable scaffold integrates readily into late-stage functionalization workflows, enabling efficient access to complex heterocyclic architectures via palladium-catalyzed coupling reactions.

Application

4-Chloro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridin-5-ol serves as a versatile building block for the construction of substituted pyrrolopyridine scaffolds. The tris(propan-2-yl)silyl group provides excellent stability and facilitates purification, while the 4-chloro and 5-hydroxyl functionalities enable sequential cross-coupling and functionalization reactions. This compound enables efficient access to biologically relevant heterocycles through palladium-catalyzed transformations and direct electrophilic substitution.

Synthesis

Route1
- In-stock
  
  651744-48-8
- ~66%
- In-stock
  
  685513-98-8
References
- L'Heureux, Alexandre; Thibault, Carl; Ruel, Rejean Tetrahedron Letters, 2004 , vol. 45, # 11 p. 2317 - 2319
Route2
- 13154-24-0
- ~%
- In-stock
  
  685513-98-8
References
- L'Heureux, Alexandre; Thibault, Carl; Ruel, Rejean Tetrahedron Letters, 2004 , vol. 45, # 11 p. 2317 - 2319
Route3
- In-stock
  
  55052-28-3
- ~%
- In-stock
  
  685513-98-8
References
- L'Heureux, Alexandre; Thibault, Carl; Ruel, Rejean Tetrahedron Letters, 2004 , vol. 45, # 11 p. 2317 - 2319

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+P364-P405-P501

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Computational Chemistry Data

TPSA 38.05
LogP 5.4189
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Organosilicon compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

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4-Chloro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridin-5-ol

CAS No. 685513-98-8

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