380358-27-0

Basic information

• Product Name: 3-[2-[(tert-butyloxycarbonyl)amino] ethyl]-5-methoxy-1H-indole
• Synonyms: 3-[2-[(tert-butyloxycarbonyl)amino] ethyl]-5-methoxy-1H-indole;5-methoxy-N'-Boc-tryptamine, 3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole, tert-butyl (2-(5-methoxy-1H-indol-3-yl)ethyl)carbamate, 3-[2-(tert-butyloxycarbonylamino)ethyl]-5-methoxy-1H-indole
• CAS NO: 380358-27-0
• Molecular Formula: C₁₆H₂₂N₂O₃
• Molecular Weight: 290
• Mol File: 380358-27-0.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-[2-[(tert-butyloxycarbonyl)amino] ethyl]-5-methoxy-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-[(tert-butyloxycarbonyl)amino] ethyl]-5-methoxy-1H-indole(380358-27-0)
• EPA Substance Registry System: 3-[2-[(tert-butyloxycarbonyl)amino] ethyl]-5-methoxy-1H-indole(380358-27-0)

Safety Data

• Hazardous Substances Data: 380358-27-0(Hazardous Substances Data)

Usage

Description

3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole is a complex organic compound characterized by a 1H-indole ring with a methoxy group at the 5 position and an ethylamine group at the 3 position, which includes a tert-butyloxycarbonyl (Boc) protecting group. This Boc group is a strategic component in chemical synthesis, facilitating selective modifications of the molecule. It is recognized for its role as a building block in the synthesis of intricate molecules, especially in the pharmaceutical industry, where its structure contributes to the creation of a variety of biologically active compounds.

Uses

Used in Pharmaceutical Development:
3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole is utilized as a key intermediate in the synthesis of pharmaceutical drugs due to its unique molecular structure. The presence of the Boc protecting group allows for the selective synthesis of complex molecules with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole is employed as a versatile building block for creating a wide array of complex organic molecules. Its structural features make it a valuable component in the development of new chemical entities with specific properties and functions.
Used in Research and Development:
3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole is also used in research settings to explore its potential applications and to understand its reactivity and behavior in various chemical reactions. This helps in advancing the knowledge of organic chemistry and contributes to the discovery of new compounds with practical applications.
Used in Drug Design:
In the drug design industry, 3-[2-[(tert-butyloxycarbonyl)amino]ethyl]-5-methoxy-1H-indole is used as a structural element in the creation of new pharmaceutical agents. Its unique features can be leveraged to design drugs with improved efficacy, selectivity, and reduced side effects.
Each application underscores the compound's importance in the realms of chemistry and medicine, highlighting its potential to contribute to the development of novel therapeutics and chemical technologies.

Upstream product

• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1430324-64-3 C₃₃H₄₀N₂O₄STe 

Relevant articles and documents

Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization to Form Functionalized Hexahydropyrido[3,4- b]Indole

A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.

Fradcarbazole A compound and preparation method and application thereof

The invention discloses a fradcarbazole A compound and a preparation method and application thereof. The fradcarbazole A compound is prepared from staurosporine or halogenated staurosporine which is subjected to a sulfur acylation reaction, a salt forming reaction together with iodomethane, a substitution reaction and a dehydrating cyclization reaction. The fradcarbazole A compound has very high selectivity and inhibitory activity on acute myeloid cell strains, namely MV4-11, with Flt3-ITD mutation, has a weak inhibiting effect on human peripheral blood mononuclear cells (PBMC), and can be developed to be an efficient and low-toxicity drug for preventing and treating leukemia.

Method for preparing spiro2-diazido-indoline

The invention provides a method for preparing a compound shown in the formula II (please see the formula in the description). The method includes the following step of making indole shown in the formula I (please see the formula in the description) react with a precursor and ceric ammonium nitrate in the inert atmosphere so that spiro2-diazido-indoline can be obtained, wherein the precursor can provide azide groups. In the formula I and the formula II, R1 is selected from at least one of hydrogen, an alkyl group of C1-C5, alkoxy of C1-C5, F, Br and Cl; R2 is an alkyl group of C1-C5; Boc represents t-butyloxycarboryl. The precursor is sodium azide or trimethylsilyl azide. The mole ratio of indole shown in the formula I to the precursor to ceric ammonium nitrate is 1:(2-4):(4-8). According to the simple method, the two azide groups are introduced to the organic molecule, and in other words, spiro2-diazido-indoline is effectively prepared under the effects of the precursor capable of providing the azide groups and ceric ammonium nitrate with indole of different structures as the raw material. The raw material is easy to prepare, the reaction condition is gentle, operation is easy and convenient, and yield can reach 45% at most.