6-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

Name: 6-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one
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CAS No. 1445993-89-4
Cat. No. CS-W000119
Purity≥95%
MDL No.None

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6-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one|CS-W000119

Structure of 1445993-89-4

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General Information

CAS No. 1445993-89-4
Cat. No. CS-W000119
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₂₅BN₂O₅S
Molecular Weight 428.31
Synonym(s) 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one(WX130459)
SMILES O=C1C(N(S(=O)(C2=CC=C(C)C=C2)=O)C=C3)=C3C(B4OC(C)(C)C(C)(C)O4)=CN1C

Description

6-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one features a boronate ester handle enabling Suzuki-Miyaura cross-coupling under mild conditions. The tosyl group enhances electrophilicity, while the tetramethyl-substituted dioxaborolane ensures stability and ease of handling. This scaffold integrates efficiently into complex heterocyclic architectures.

Application

6-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling with aryl and heteroaryl halides under mild conditions. The tosyl group provides enhanced stability and orthogonality in multi-step syntheses, while the pyrrolo[2,3-c]pyridin-7-one core offers a rigid, functionalized scaffold suitable for medicinal chemistry applications requiring precise structural control and ease of purification.

Safety Information

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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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 79.53
LogP 2.18462
H_Acceptors 7
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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6-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

CAS No. 1445993-89-4

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