290331-71-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(TERT-BUTOXYCARBONYL)-5-METHOXY-1H-INDOL-2-YLBORONIC ACID is used as a reactant for the preparation of various biologically active compounds. Its unique structure allows it to be a key intermediate in the synthesis of pharmaceuticals with potential therapeutic applications.
Used in Chemical Synthesis:
1-(TERT-BUTOXYCARBONYL)-5-METHOXY-1H-INDOL-2-YLBORONIC ACID is used as a reactant for the preparation of dihalogenated pyrazoles via dipolar cycloaddition by palladium-catalyzed cross-coupling processes. This makes it a valuable compound in the development of new chemical entities with potential applications in various fields.
Used in Organic Chemistry:
In the field of organic chemistry, 1-(TERT-BUTOXYCARBONYL)-5-METHOXY-1H-INDOL-2-YLBORONIC ACID is used as a reactant for Suzuki-Miyaura cross-coupling reactions. These reactions are widely employed in the synthesis of complex organic molecules, including those with potential applications in materials science, pharmaceuticals, and agrochemicals.
Used in Natural Product Synthesis:
1-(TERT-BUTOXYCARBONYL)-5-METHOXY-1H-INDOL-2-YLBORONIC ACID is used as a reactant for the synthesis of the isocryptolepine alkaloid and its related skeletons using a modified Pictet-Spengler reaction. This application highlights its potential in the development of novel natural products with diverse biological activities.

InChI:InChI=1/C14H18BNO5/c1-14(2,3)21-13(17)16-11-6-5-10(20-4)7-9(11)8-12(16)15(18)19/h5-8,18-19H,1-4H3

Upstream product

• 99275-47-5 1-(tert-butyloxycarbonyl)-5-methoxyindole 
• 1006-94-6 5-methoxylindole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 944707-84-0 C₂₉H₃₀N₂O₅S 
• 1235344-31-6 3-bromo-5-[N-Boc-5-methoxyindol]-2-yl-1-(4-methoxyphenyl)-1H-pyrazole 
• 7699-18-5 5-methoxyindolin-2-one 
• 1352124-35-6 N-Boc-2-(cyclopenten-1-yl)-5-methoxyindole 
• 99275-47-5 1-(tert-butyloxycarbonyl)-5-methoxyindole 
• 1370525-29-3 C₂₉H₃₁NO₅ 
• 1369594-77-3 C₂₀H₁₉ClN₂O₅ 
• 1369594-78-4 C₁₅H₁₃ClN₂O 
• 1428884-68-7 potassium (1-((tert-butoxy)carbonyl)-5-methoxy-1H-indol-2-yl)trifluoroboranuide 
• 1426961-82-1 tert-butyl 5-methoxy-2-(6-((2S,3S)-3-methyl-4-oxo-3-phenyloxetan-2-yl)pyridin-2-yl)-1H-indole-1-carboxylate 
• 906779-78-0 2-(3-chlorophenyl)-5-methoxy-1H-indole 

Relevant academic research and scientific papers

FUSED AZOLE DERIVATIVE

The present invention provides agents for treating or preventing diseases such as mood disorder, anxiety disorder, schizophrenia, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastrointestinal disease, drug addiction, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, head injury, inflammation, immune-related disease, alopecia. Specifically, the invention provides fused azole derivatives represented by general formula (I) or pharmaceutically acceptable salts thereof that have an antagonistic action against the arginine-vasopressin 1b receptor:

CYCLOHEXYL AMIDE DERIVATIVES AS CRF RECEPTOR ANTAGONISTS

There are described cydohexyl amide derivatives useful as corticotropin releasing factor (CRF) receptor antagonists

Trisoxazoline/Cu(II)-catalyzed asymmetric intramolecular Friedel-Crafts alkylation reaction of indoles

Intramolecular Friedel-Crafts alkylation reaction of indoles catalyzed by trisoxazoline/copper(II) is described. This annulation provides an easy access to polycyclic indole derivatives with up to 90% ee in up to 99% yield.

Fluorescent pyrimidopyrimidoindole nucleosides: Control of photophysical characterizations by substituent effects

(Chemical Equation Presented) 10-(2-Deoxy-β-D-ribofuranosyl) pyrimido[4′,5′:4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dC PPI) and its derivatives were synthesized via the Suzuki-Miyaura coupling reaction of 5-iododeoxycytidine with 5-substituted N-Boc-indole-2- borates and characterized by UV-vis and fluorescence spectroscopy. The new fluorescent nucleosides showed rather large Stokes shifts (116-139 nm) in an aqueous buffer. The fluorescent intensities were dependent on the nature of the substituents on the indole rings. The electron-withdrawing groups increased the fluorescent intensity while the electron-donating groups having lone pairs decreased it. Among the substituted dCPPI derivatives tested, the trimethylammonium derivative of dCPPI was found to emit the brightest fluorescent light. The solvatochromism of dCPPI and its derivatives was also studied. Some of the dCPPI derivatives showed interesting solvent-dependent fluorescence enhancement and could be useful as new fluorescent structural probes for nucleic acids. The Lippert-Mataga analyses of the Stokes shift were also carried out to obtain estimated values of the dipole moment of the excited states of some of the derivatives.

Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin

The compounds of the present invention are represented by the chemical structure found in Formula (I): wherein: the carbon atom designated * is in the R or S configuration; and X is a fused bicyclic carbocycle or heterocycle selected from the group consisting of benzofuranyl, benzo[b]thiophenyl, benzoisothiazolyl, benzoisoxazolyl, indazolyl, indolyl, isoindolyl, indolizinyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, imidazo[1,2-a]pyridinyl, pyrazolo[1,5-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[2,3-b]pyridinyl, thieno[3,2-b]pyridinyl, 1H-pyrrolo[2,3-b]pyridinyl, indenyl, indanyl, dihydrobenzocycloheptenyl, tetrahydrobenzocycloheptenyl, dihydrobenzothiophenyl, dihydrobenzofuranyl, indolinyl, naphthyl, tetrahydronaphthyl, quinolinyl, isoquinolinyl, 4H-quinolizinyl, 9aH-quinolizinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, benzo[1,2,3]triazinyl, benzo[1,2,4]triazinyl, 2H-chromenyl, 4H-chromenyl, and a fused bicyclic carbocycle or fused bicyclic heterocycle optionally substituted with substituents (1 to 4 in number) as defined in R14; with R1, R2, R3, R4, R5, R6, R7, R8, and R14 defined herein.

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%).

A versatile and convenient method for the synthesis of substituted benzo[a]carbazoles and pyrido[2,3-a]carbazoles

Treatment of 2-(o-tolyl)- or 2-(3-methyl-2-pyridyl)-substituted indole-3-carbaldehydes with potassium tert-butoxide in DMF at 70-80°C with simultaneous irradiation from a 400 W high-pressure mercury lamp afforded benzo[a]carbazoles and pyrido[2,3-a]carbaz