1-(Tetrahydropyran-2-yl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indazole

Name: 1-(Tetrahydropyran-2-yl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indazole
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 956388-05-9
Cat. No. CS-M0441
Purity≥95%
MDL No.MFCD18207194

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1-(Tetrahydropyran-2-yl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indazole|CS-M0441

Structure of 956388-05-9

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General Information

CAS No. 956388-05-9
Cat. No. CS-M0441
Purity ≥95%
MDL No. MFCD18207194
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₅BN₂O₃
Molecular Weight 328.21
Synonym(s) 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole
SMILES CC1(C)C(C)(C)OB(C2=CC=CC3=C2C=NN3C4CCCCO4)O1

Description

This boronate ester integrates a tetrahydropyran-2-yl protected indazole core, enabling stable handling and orthogonal deprotection. The tetramethylboronate moiety facilitates efficient Suzuki-Miyaura coupling under mild conditions, delivering functionalized indazoles with high chemoselectivity.

Application

1-(Tetrahydropyran-2-yl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indazole serves as a stable, bench-ready boron building block for Suzuki-Miyaura coupling reactions. The tetrahydropyranyl group provides protection of the indazole nitrogen, enhancing solubility and stability while enabling orthogonal deprotection. The pinacol borane moiety facilitates efficient cross-coupling with aryl and vinyl halides under mild conditions, making it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science workflows.

Synthesis

Route1
- In-stock
  
  1022158-35-5
- In-stock
  
  73183-34-3
- ~88%
- In-stock
  
  956388-05-9
References
- Crestey, Francois; Lohou, Elodie; Stiebing, Silvia; Collot, Valerie; Rault, Sylvain Synlett, 2009 , # 4 p. 615 - 619
Route2
- 1137278-45-5
- In-stock
  
  73183-34-3
- ~99%
- In-stock
  
  956388-05-9
References
- GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG Patent: WO2009/146406 A1, 2009 ; Location in patent: Page/Page column 66-67 ; WO 2009/146406 A1
Route3
- 956388-08-2
- In-stock
  
  73183-34-3
- ~67%
- In-stock
  
  956388-05-9
References
- GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG Patent: WO2009/146406 A1, 2009 ; Location in patent: Page/Page column 68-69 ; WO 2009/146406 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

Quality Control

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Computational Chemistry Data

TPSA 45.51
LogP 3.0346
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indazole compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Tetrahydropyran compounds

Key Words

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1-(Tetrahydropyran-2-yl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indazole

CAS No. 956388-05-9

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