tert-Butyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Name: tert-Butyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate
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CAS No. 928653-80-9
Cat. No. CS-0063925
Purity≥97%
MDL No.None

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tert-Butyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate|CS-0063925

Structure of 928653-80-9

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General Information

CAS No. 928653-80-9
Cat. No. CS-0063925
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₃BrN₂O₂
Molecular Weight 297.15
Synonym(s) tert-butyl 5-bromopyrrolo[2,3-b]pyridine-1-carboxylate
SMILES O=C(N1C=CC2=CC(Br)=CN=C21)OC(C)(C)C

Description

tert-Butyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate features a brominated pyrrolopyridine core with a bench-stable tert-butyl ester handle. This electrophilic scaffold enables direct coupling in cross-coupling reactions, facilitating rapid access to complex heterocycles. The electron-deficient aryl bromide integrates cleanly into Pd-catalyzed transformations under standard conditions.

Application

tert-Butyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate serves as a versatile building block for the synthesis of substituted pyrrolopyridine scaffolds. The bromine substituent enables palladium-catalyzed cross-coupling reactions, while the tert-butyl ester group offers stability and convenient deprotection under mild acidic conditions. This compound facilitates efficient access to biologically relevant heterocycles in medicinal chemistry and materials science applications.

Synthesis

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  928653-80-9
References
- Organic and Biomolecular Chemistry, , vol. 9, # 14 p. 5129 - 5136
Route2
- In-stock
  
  24424-99-5
- In-stock
  
  183208-35-7
- ~%
- In-stock
  
  928653-80-9
References
- Merkul, Eugen; Klukas, Fabian; Dorsch, Dieter; Graedler, Ulrich; Greiner, Hartmut E.; Mueller, Thomas J. J. Organic and Biomolecular Chemistry, 2011 , vol. 9, # 14 p. 5129 - 5136

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
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

TPSA 44.12
LogP 3.582
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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tert-Butyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

CAS No. 928653-80-9

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