benzyl 4-[5-bromo-6-[(1S)-1-methoxyethyl]-3-pyridyl]piperazine-1-carboxylate
[CAS# 2641451-78-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: benzyl 4-[5-bromo-6-[(1S)-1-methoxyethyl]-3-pyridyl]piperazine-1-carboxylate
• Synonyms: benzyl (S)-4-(5-bromo-6-(1-methoxyethyl)pyridin-3-yl)piperazine-1-carboxylate
• Molecular Formula: C₂₀H₂₄BrN₃O₃
• Molecular Weight: 434.33
• CAS Registry Number: 2641451-78-5
• SMILES: C[C@@H](C1=C(C=C(C=N1)N2CCN(CC2)C(=O)OCC3=CC=CC=C3)Br)OC

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 544.5±50.0 °C 760 mmHg (Calc.)^*
• Flash point: 283.1±30.1 °C (Calc.)^*
• Index of refraction: 1.592 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

Benzyl 4-[5-bromo-6-[(1S)-1-methoxyethyl]-3-pyridyl]piperazine-1-carboxylate is a chiral, brominated pyridine derivative functionalized with a piperazine and a benzyl carbamate group. The molecule consists of a pyridine ring substituted at the 6-position with an (S)-configured 1-methoxyethyl group, a bromine atom at the 5-position, and a piperazine unit linked via the 4-position of the pyridine. The piperazine nitrogen is protected as a benzyl carbamate, providing stability and a handle for further synthetic elaboration. This combination of stereochemistry, heteroaryl substitution, and protecting group functionality makes it a versatile intermediate in medicinal chemistry, particularly for the synthesis of small-molecule drug candidates.

The bromine substituent on the pyridine ring allows selective cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, and other palladium-catalyzed transformations, enabling the installation of diverse aryl or heteroaryl fragments. The stereogenic methoxyethyl side chain maintains the three-dimensional orientation of the molecule, which is important for stereospecific interactions in subsequent target molecules. The benzyl carbamate on the piperazine nitrogen can be removed under hydrogenolysis conditions to reveal the free amine for further coupling or functionalization, allowing modular design of pharmacologically relevant structures.

This intermediate is typically employed in multi-step synthetic routes where chirality, functional group compatibility, and late-stage derivatization potential are required. It enables the introduction of the pyridyl-piperazine motif, which is common in compounds targeting central nervous system receptors, kinases, or other protein targets in drug discovery programs. Handling of this compound requires standard precautions for chiral and halogenated heteroaromatic compounds, including storage under inert atmosphere and protection from moisture to preserve stereochemical integrity and prevent undesired reactions.