1313026-17-3

Basic information

• Product Name: (1-tosyl-1H-indol-2-yl)boronic acid MIDA ester
• Synonyms: (1-tosyl-1H-indol-2-yl)boronic acid MIDA ester
• CAS NO: 1313026-17-3
• Molecular Weight: 426.258
• Mol File: 1313026-17-3.mol

Chemical Properties

• CAS DataBase Reference: (1-tosyl-1H-indol-2-yl)boronic acid MIDA ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1-tosyl-1H-indol-2-yl)boronic acid MIDA ester(1313026-17-3)
• EPA Substance Registry System: (1-tosyl-1H-indol-2-yl)boronic acid MIDA ester(1313026-17-3)

Safety Data

• Hazardous Substances Data: 1313026-17-3(Hazardous Substances Data)

Upstream product

• 1104637-53-7 B-ethynyl N-methyliminodiacetic acid boronate 
• 61613-20-5 N-tosyl-2-iodoaniline 
• 1313026-16-2 C₂₀H₁₉BN₂O₆S 

Downstream Products

• 1312936-82-5 1-tosyl-2-(4'-tert-butylphenyl)indole 
• 1312936-83-6 2-(4-trifluoromethylphenyl)-1-[(4-methylphenyl)sulfonyl]-1H-indole 
• 107734-06-5 N-tosyl-2-phenylindole 
• 1429481-71-9 1-(toluene-4-sulfonyl)-1,3-dihydro-indol-2-one 
• 13861-75-1 spiro[cyclopropane-1,3'-indolin]-2'-one 
• 59-48-3 2-oxoindole 

Relevant articles and documents

Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(i)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols

A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(i)/Pd(0)/Cu(ii) catalysis. 2-Iodoanilines and phenols undergo a Cu(i)/Pd(0)-catalyzed Sonogashira reaction with ethynyl BMIDA followed by in situ Cu(ii)-catalyzed 5-endo-dig cyclization to generate heterocyclic scaffolds with a BMIDA functional group in the 2-position. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

Pd-catalysed C-C bond formation is an essential tool within the pharmaceutical and agrochemical industries. Many of these reactions rely heavily on polar aprotic solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (Cyrene) in Sonogashira cross-coupling and Cacchi-type annulations.

Tandem cycloisomerization/Suzuki coupling of arylethynyl MIDA boronates

A tandem gold-catalyzed cycloisomerization/Suzuki cross-coupling sequence involving arylethynyl-N-methyliminodiacetic acid boronates is described. Combining the mildness of homogeneous gold catalysis with the versatility of N-methyliminodiacetic acid (MID