(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate

Name: (R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate
Brand: ChemScene
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CAS No. 143322-56-9
Cat. No. CS-M3330
Purity≥98%
MDL No.MFCD09835149

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(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate|CS-M3330

Structure of 143322-56-9

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Description

(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate is a stereochemically defined building block featuring a brominated indole moiety tethered to a pyrrolidine ring via a carbonyl linker. This configuration enables direct incorporation into complex heterocyclic scaffolds under mild coupling conditions, offering enhanced regioselectivity in synthetic sequences. The benzyl ester group provides convenient deprotection pathways, while the electron-deficient bromoindole facilitates downstream functionalization through transition-metal-catalyzed cross-coupling reactions.

Application

(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate serves as a versatile chiral building block for the synthesis of indole-containing peptidomimetics and heterocyclic scaffolds. The bromo-substituted indole moiety enables subsequent palladium-catalyzed cross-coupling reactions, while the pyrrolidine carboxylate group offers orthogonal functionalization potential. Bench-stable and amenable to standard purification methods, it facilitates efficient access to complex molecular architectures in medicinal chemistry campaigns.

General Information

CAS No. 143322-56-9
Cat. No. CS-M3330
Purity ≥98%
MDL No. MFCD09835149
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₁₉BrN₂O₃
Molecular Weight 427.29
Synonym(s) (R)-3-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole; Benzyl (2R)-2-[(5-bromo-1H-indol-3-yl)carbonyl]pyrrolidine-1-carboxylate
SMILES BrC1=CC=C(NC=C2C([C@@H]3N(C(OCC4=CC=CC=C4)=O)CCC3)=O)C2=C1

Computational Chemistry Data

TPSA 62.4
LogP 4.9143
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 4

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate

CAS No. 143322-56-9

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