benzyl (S)-4-(5-(5-bromo-3-(3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropyl)-1-ethyl-1H-indol-2-yl)-6-(1-methoxyethyl)pyridin-3-yl)piperazine-1-carboxylate
[CAS# 2641451-81-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: benzyl (S)-4-(5-(5-bromo-3-(3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropyl)-1-ethyl-1H-indol-2-yl)-6-(1-methoxyethyl)pyridin-3-yl)piperazine-1-carboxylate
• Synonyms: benzyl 4-[5-[5-bromo-3-[3-[tert-butyl(diphenyl)silyl]oxy-2,2-dimethylpropyl]-1-ethylindol-2-yl]-6-[(1S)-1-methoxyethyl]-3-pyridinyl]piperazine-1-carboxylate
• Molecular Formula: C₅₁H₆₁BrN₄O₄Si
• Molecular Weight: 902.04
• CAS Registry Number: 2641451-81-0
• SMILES: CCN1C2=C(C=C(C=C2)Br)C(=C1C3=C(N=CC(=C3)N4CCN(CC4)C(=O)OCC5=CC=CC=C5)[C@H](C)OC)CC(C)(C)CO[Si](C6=CC=CC=C6)(C7=CC=CC=C7)C(C)(C)C

Discovery and Applications

Benzyl (S)-4-(5-(5-bromo-3-(3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropyl)-1-ethyl-1H-indol-2-yl)-6-(1-methoxyethyl)pyridin-3-yl)piperazine-1-carboxylate is a highly functionalized chiral intermediate used in medicinal chemistry for the synthesis of complex small-molecule drug candidates. The compound contains a pyridine ring substituted at the 6-position with an (S)-configured 1-methoxyethyl group and at the 5-position with a brominated indole derivative bearing a 3-(3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropyl) side chain. The pyridine is linked via the 3-position to a piperazine unit protected as a benzyl carbamate. This combination of stereochemistry, halogenation, silyl protection, and heterocyclic motifs allows precise modular functionalization in synthetic sequences.

The bromine on the indole and pyridine rings serves as a reactive site for palladium-catalyzed cross-coupling reactions, enabling the attachment of aryl or heteroaryl fragments while maintaining stereochemical integrity. The tert-butyldiphenylsilyl-protected hydroxyl group provides temporary masking of the alcohol functionality, permitting selective deprotection under mild conditions when further derivatization is required. The benzyl carbamate on the piperazine nitrogen can be removed by hydrogenolysis to expose the free amine for subsequent coupling reactions, facilitating incorporation into larger, biologically active scaffolds.

This intermediate is typically employed in multi-step medicinal chemistry routes to introduce the pyridyl-indole-piperazine framework with defined stereochemistry and functional group compatibility. It enables late-stage diversification for structure-activity relationship studies, particularly in programs targeting kinases, CNS receptors, or other protein targets where heteroaryl and chiral side chains influence binding affinity and pharmacokinetic properties. Handling requires standard precautions for chiral, halogenated, and silyl-protected intermediates, including storage under inert atmosphere and protection from moisture to preserve functional group integrity and stereochemical purity.