475102-14-8

Usage

Uses

Used in Pharmaceutical Industry:
1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID is used as a building block for the synthesis of various pharmaceuticals. Its boronic acid functionality allows for the formation of carbon-carbon bonds through Suzuki-Miyaura cross-coupling reactions, enabling the creation of complex organic molecules with potential therapeutic applications.
Used in Agrochemical Industry:
1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID is used as a precursor in the synthesis of agrochemicals. Its versatility in organic synthesis and ability to form carbon-carbon bonds make it a valuable compound for the development of new agrochemicals with improved properties and efficacy.
Used in Organic Synthesis:
1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID is used as a versatile intermediate in organic synthesis. Its BOC protecting group can be removed under mild conditions, allowing for further functionalization and modification of the molecule. This makes it a valuable building block for the preparation of complex organic molecules with diverse applications in various industries.

InChI:InChI=1/C14H18BNO4/c1-9-5-6-11-10(7-9)8-12(15(18)19)16(11)13(17)20-14(2,3)4/h5-8,18-19H,1-4H3

Upstream product

• 614-96-0 5-methyl-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 129822-49-7 5-methylindole-1-carboxylic acid tert-butyl ester 

Downstream Products

• 1356140-72-1 β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose-3-(2-cyanoethyl N,N-diisopropylphosphoramidite) 
• 1356140-71-0 β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose 
• 944707-85-1 C₂₉H₃₀N₂O₄S 

Relevant academic research and scientific papers

DNA duplexes and triplex-forming oligodeoxynucleotides incorporating modified nucleosides forming stable and selective triplexes

We have previously reported DNA triplexes containing the unnatural base triad G-PPI·C3, in which PPI is an indole-fused cytosine derivative incorporated into DNA duplexes and C3 is an abasic site in triplex-forming oligonucleotides (TFOs) introduced by a propylene linker. In this study, we developed a new unnatural base triad A-ψ·CR1 where ψ and CR1 are base moieties 2′-deoxypseudouridine and 5-substituted deoxycytidine, respectively. We examined several electron-withdrawing substituents for R1 and found that 5-bromocytosine (C Br) could selectively recognize ψ. In addition, we developed a new PPI derivative, PPIMe, having a methyl group on the indole ring in order to achieve selective triplex formation between DNA duplexes incorporating various Watson-Crick base pairs, such as T-A, C-G, A-ψ, and G-PPIMe, and TFOs containing T, C, CBr, and C3. We studied the selective triplex formation between these duplexes and TFOs using UV-melting and gel mobility shift assays.

A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols

2-Indolyl borates are prepared via addition of LDA to a mixture of N-Bo-indole and triisopropyl borate at 0-5 °C. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).