tert-Butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate

Name: tert-Butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate
Brand: ChemScene
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CAS No. 864770-82-1
Cat. No. CS-0085367
Purity≥97%
MDL No.MFCD13195073

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tert-Butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate|CS-0085367

Structure of 864770-82-1

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General Information

CAS No. 864770-82-1
Cat. No. CS-0085367
Purity ≥97%
MDL No. MFCD13195073
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₉H₂₇BN₂O₄
Molecular Weight 358.24
Synonym(s) 1-N-Boc-3-methyl-indazole-5-boronic acid pinacol ester
SMILES O=C(N1N=C(C)C2=C1C=CC(B3OC(C)(C)C(C)(C)O3)=C2)OC(C)(C)C

Description

tert-Butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate delivers a boronate-functionalized indazole scaffold with enhanced stability and solubility. This bench-stable reagent integrates readily into Suzuki-Miyaura coupling protocols, enabling efficient C–C bond formation under mild conditions. The tetramethyl-substituted dioxaborolane moiety ensures high functional group tolerance and compatibility with diverse reaction environments.

Application

tert-Butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate serves as a versatile boron-containing building block for Suzuki-Miyaura coupling reactions. The indazole core provides a rigid, bioactive scaffold commonly found in pharmaceuticals, while the tert-butyl ester offers stability and ease of deprotection. The pinacol boronate group enables efficient cross-coupling under mild conditions, with excellent functional group tolerance and bench stability, making it ideal for iterative synthesis in medicinal chemistry and API development workflows.

Synthesis

Route1
- In-stock
  
  552331-49-4
- In-stock
  
  73183-34-3
- ~95%
- In-stock
  
  864770-82-1
References
- ALCON MANUFACTURING, LTD. Patent: US2008/153813 A1, 2008 ; Location in patent: Page/Page column 24 ; US 20080153813 A1

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

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Computational Chemistry Data

TPSA 62.58
LogP 3.42712
H_Acceptors 6
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indazole compounds

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tert-Butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate

CAS No. 864770-82-1

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