1-[5-bromo-6-[(1S)-1-methoxyethyl]-3-pyridyl]-4-methyl-piperazine
[CAS# 2940879-42-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Piperazine
• Name: 1-[5-bromo-6-[(1S)-1-methoxyethyl]-3-pyridyl]-4-methyl-piperazine
• Molecular Formula: C₁₃H₂₀BrN₃O
• Molecular Weight: 314.22
• CAS Registry Number: 2940879-42-3
• SMILES: C[C@@H](C1=C(C=C(C=N1)N2CCN(CC2)C)Br)OC

Discovery and Applications

1-[5-bromo-6-[(1S)-1-methoxyethyl]-3-pyridyl]-4-methyl-piperazine is a chiral, brominated pyridine derivative widely used as an intermediate in medicinal chemistry for the construction of heteroaryl-containing drug candidates. The compound consists of a pyridine ring substituted at the 6-position with an (S)-configured 1-methoxyethyl group and at the 5-position with a bromine atom, providing a reactive site for further functionalization. The pyridine is connected via the 3-position to a 1-methylpiperazine unit, offering a basic nitrogen that can participate in additional reactions or serve as part of the pharmacophore in target molecules. The defined stereochemistry and halogen functionality make this intermediate suitable for stereocontrolled, modular assembly of complex drug-like structures.

The bromine atom on the pyridine allows palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura or Buchwald–Hartwig aminations, facilitating the introduction of diverse aryl, heteroaryl, or alkyl fragments while retaining stereochemical integrity. The methoxyethyl side chain provides a stereodefined handle for further transformations, and the piperazine nitrogen can participate in functionalizations including alkylation or carbamate formation. This intermediate is often employed in multi-step synthetic routes where chirality, functional group compatibility, and late-stage diversification are important, particularly in programs targeting CNS receptors, kinases, or other biologically relevant proteins.

Proper handling involves standard precautions for chiral and halogenated heteroaryl compounds. The compound is typically supplied as a high-purity solid and should be stored under inert atmosphere to prevent degradation or racemization. Analytical techniques such as chiral HPLC, NMR spectroscopy, and mass spectrometry are used to verify stereochemistry, purity, and structural integrity prior to further synthetic use.