148249-36-9

Usage

Uses

Used in Organic Synthesis:
3-Bromo-1-(triisopropylsilyl)indole is used as a starting material for the synthesis of various organic compounds. The triisopropylsilyl group offers steric hindrance and resistance to a range of reactions, making it an effective protective group for the indole ring. The bromine atom, on the other hand, acts as a good leaving group, allowing synthetic chemists to manipulate and form a wide array of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Bromo-1-(triisopropylsilyl)indole is used as an intermediate in the synthesis of various drug molecules. Its unique structure and reactivity make it a valuable building block for the development of new therapeutic agents, particularly in the area of medicinal chemistry.
Used in Research and Development:
3-Bromo-1-(triisopropylsilyl)indole is also utilized in academic and industrial research settings as a model compound for studying the reactivity and properties of indole derivatives. Its presence in various chemical reactions provides insights into the underlying mechanisms and helps in the design of new synthetic strategies and methodologies.

InChI:InChI=1/C17H26BrNSi/c1-12(2)20(13(3)4,14(5)6)19-11-16(18)15-9-7-8-10-17(15)19/h7-14H,1-6H3

Upstream product

• 123191-00-4 1-(triisopropylsilyl)-1H-indole 
• 120-72-9 indole 
• 13154-24-0 triisopropylsilyl chloride 
• 146886-51-3 1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine 

Downstream Products

• 123191-00-4 1-(triisopropylsilyl)-1H-indole 
• 327163-16-6 1-triisopropylsilyl-3-(4-nitro-1,3-butadienyl)indole 
• 135531-86-1 camalexin 
• 208655-73-6 (1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid 
• 1504-16-1 3-phenyl-1H-indole 
• 727416-65-1 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole 
• 83-34-1 3-Methylindole 
• 487-89-8 Indole-3-carboxaldehyde 
• 526-55-6 2-(3-indole)-ethanol 
• 15224-25-6 3-benzoylindole 
• 181780-84-7 Phenyl-(1-triisopropylsilanyl-1H-indol-3-yl)-methanone 
• 1484-19-1 3-ethyl-1H-indole 
• 725252-08-4 (+)-(2R,5R,6R)-5-isopropyl-2-methyl-6-(3-indolyl)-2-vinylcyclohexanone 

Relevant academic research and scientific papers

Direct C-3 lithiation of 1-(triisopropylsilyl)indole

1-(Triisopropylsilyl)indole can be directly lithiated at 3-position with tert-BuLi-TMEDA in hexane at 0°C for 3 h. The generated lithio species is reacted with a variety of electrophiles to give 3-substituted 1-(triisopropylsilyl)indoles in good yields.

4-Substituted Pyrrolo[2,3-d]pyrimidine Compound and Use Thereof

The invention relates to a 4-substituted pyrrolo[2,3-d]pyrimidine compound and the use thereof in preparing medications for treating JAK-targeted diseases such as rheumatoid, immune system diseases, and tumor. The 4-substituted pyrrolo[2,3-d]pyrimidine compound of the invention is as shown in chemical formula I. The activity experimental results of the invention show that the new compound has obvious effect and activity in inhibition of Janus kinases, JAK-STAT, cell proliferation of human lymphocytoma, and rheumatoid arthritis.

NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE

Provided are a nitrogen-containing aromatic heterocyclic compound useful as an organic semiconductor material and an organic electronic device using this compound. The nitrogen-containing aromatic heterocyclic compound has a fused indole skeleton represented by the following formula (1), the organic semiconductor material contains the said compound, and the organic electronic device uses the said organic semiconductor material. In general formula (1), X is N-A', O, S, or Se; A is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more; and R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more.

NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE

Provided are a novel nitrogen-containing aromatic heterocyclic compound and an organic electronic device using the compound. This nitrogen-containing aromatic compound is represented by the general formula (1). Further, the present invention relates to or

Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: Asymmetric synthesis of allyl oxindoles

The first catalytic, enantioselective Meerwein-Eschenmoser Claisen rearrangement has been achieved. Palladium(II) BINAP or phosphinooxazoline catalysts were employed to generate oxindole products with 100% conversion and up to 92% ee. Copyright

Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.

[reaction: see text] In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields.

Reactions of a nitrodienamine with 1-protected indolyllithium

Reactions of a nitrodienamine (1) with indolyllithiums prepared from 1-protected indole derivatives were investigated.

A Highly Enantioselective Asymmetric Hydrogenation Route to β-(2R,3S)-Methyltryptophan

Asymmetric hydrogenation of a protected (Z)-dehydro-β-methyltryptophan derivative 2 with (R,R)-Me-DuPHOS-Rh catalysis was achieved in 97percent ee.Deprotection then afforded (2R,3S)-β-methyltryptophan 1.

3-lithio-1-(triisopropylsilyl)indole, preparation and reactions with electrophilic reagents

3-Lithio-1-(triisopropylsilyl)indole (2) is prepared by halogenmetal exchange from the corresponding 3-bromoindole and regioselectively reacts with a variety of electrophilic reagents to give 3-substituted indoles.

Total Synthesis of Grossularines-1 and -2

The first total syntheses of grossularines-1 (1a) and -2 (1b) have been completed.The cross-coupling reaction between ethyl 3-iodoindole-2-carboxylate (6) and the directed metalation-derived imidazole 9b gave the ethyl 3-(5-imidazolyl)indole-2-carboxylate 11b.Hydrolysis of the ester group of 11b, followed by Curtius rearrangement, yielded the 2-isocyanatoindole 13b.The thermal electrocyclic reaction of 13b was carried out to provide the desired tetracyclic pyridoindole ring system 14b, which was converted into the triflate 15b.The three-component cross-coupling reaction of the triflate 15b, carbon monoxide, and p-(OMOM)phenylboronic acid (17) followed by hydrolysis gave glossularine-2 (1b) in low yield.In addition, the palladium-catalyzed carbonylation of the triflate 15b afforded the N-deprotected methyl ester 19a or the methyl ester 19b depending on the amounts of triethylamine used.Compound 19a was treated with either p-(OMOM)phenyllithium or 3-(N-TIPS)indolyllithium to obtain grossularine-2 (1b) and grossularine-1 (1a) (37percent), respectively.By contrast, when 19b was treated with the same aryllithium reagents, grossularine-2 (1b) (51percent) and grossularine-1 (1a) (63percent) were produced, respectively.