tert-butyl 4-[5-bromo-6-[(1S)-1-methoxyethyl]pyridin-3-yl]piperazine-1-carboxylate
[CAS# 2641824-76-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-butyl 4-[5-bromo-6-[(1S)-1-methoxyethyl]pyridin-3-yl]piperazine-1-carboxylate
• Synonyms: 2-Methyl-2-propanyl 4-{5-bromo-6-[(1S)-1-methoxyethyl]-3-pyridinyl}-1-piperazinecarboxylate
• Molecular Formula: C₁₇H₂₆BrN₃O₃
• Molecular Weight: 400.31
• CAS Registry Number: 2641824-76-0
• SMILES: C[C@@H](C1=C(C=C(C=N1)N2CCN(CC2)C(=O)OC(C)(C)C)Br)OC

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 472.8±45.0 °C 760 mmHg (Calc.)^*
• Flash point: 239.8±28.7 °C (Calc.)^*
• Index of refraction: 1.544 (Calc.)^*

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

Discovery and Applications

Tert-butyl 4-[5-bromo-6-[(1S)-1-methoxyethyl]pyridin-3-yl]piperazine-1-carboxylate is a chiral, halogenated pyridine derivative widely used as an intermediate in medicinal chemistry. The compound features a pyridine ring substituted at the 6-position with an (S)-configured 1-methoxyethyl group and at the 5-position with a bromine atom, which provides a reactive site for further functionalization. The pyridine ring is linked at the 3-position to a piperazine unit protected as a tert-butyl carbamate, offering stability and selective deprotection opportunities for downstream transformations. The defined stereochemistry and protecting group strategy make this intermediate suitable for the assembly of complex drug-like molecules.

The bromine atom on the pyridine ring enables palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings, allowing the introduction of diverse aryl, heteroaryl, or alkynyl groups. The methoxyethyl side chain provides a stereodefined handle that maintains three-dimensional structure critical for biological activity in final molecules. The tert-butyl carbamate on the piperazine nitrogen can be selectively removed under acidic conditions to reveal the free amine for further coupling, facilitating modular design of pharmacologically active compounds.

This intermediate is commonly employed in multi-step synthetic sequences where chirality, functional group compatibility, and late-stage diversification are required. Its utility is particularly significant in programs exploring central nervous system targets, kinase inhibitors, and other heteroaryl-containing drug candidates. Proper handling and storage under inert atmosphere are recommended to maintain stereochemical integrity and prevent hydrolysis or deprotection of the sensitive functional groups.