99275-47-5

Basic information

• Product Name: 1-BOC-5-METHOXYINDOLE
• Synonyms: N-BOC-5-METHOXYINDOLE;TERT-BUTYL 5-METHOXY-1H-INDOLE-1-CARBOXYLATE;1-BOC-5-METHOXYINDOLE;5-Methoxy-1H-indole, N-BOC protected;5-Methoxy-1H-indole, N-BOC protected 98%;N-(tert-Butoxycarbonyl)-5-methoxyindole;5-Methoxyindole-1-carboxylic acid tert-butyl ester;5-Methoxy-1H-indole,N-BOCprotected98%
• CAS NO: 99275-47-5
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.29
• Product Categories: blocks;IndolesOxindoles;Indoline & Oxindole;Building Blocks;C13 to C27;Chemical Synthesis;Heterocyclic Building Blocks;Indoles
• Mol File: 99275-47-5.mol

Chemical Properties

• Melting Point: 82-85
• Boiling Point: 357.34 °C at 760 mmHg
• Flash Point: 169.913 °C
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 1-BOC-5-METHOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-5-METHOXYINDOLE(99275-47-5)
• EPA Substance Registry System: 1-BOC-5-METHOXYINDOLE(99275-47-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 99275-47-5(Hazardous Substances Data)

Usage

Uses

1-BOC-5-METHOXYINDOLE is used as a reactant for the preparation of several specialized compounds and materials in the fields of organic chemistry and pharmaceuticals. Its applications include:
Used in Organic Synthesis:
1-BOC-5-METHOXYINDOLE is used as a reactant for asymmetric intramolecular Friedel-Crafts alkylation reactions, which are important for the synthesis of complex organic molecules with specific stereochemistry.
Used in Palladium-Catalyzed Reactions:
In palladium-catalyzed carboaminoxylations with arylboronic acids and TEMPO catalysts, 1-BOC-5-METHOXYINDOLE serves as a reactant to form various organic compounds with potential applications in pharmaceuticals and materials science.
Used in Fluorescent Compounds Synthesis:
1-BOC-5-METHOXYINDOLE is used as a reactant in the synthesis of fluorescent pyrimidopyrimidoindole nucleosides via Suzuki-Miyaura coupling reactions. These fluorescent compounds have potential applications in bioimaging and diagnostics.
Used in Peptide Synthesis:
1-BOC-5-METHOXYINDOLE is used as a reactant for the preparation of novel conformationally restricted βand γ-amino acids, which are valuable building blocks in peptide synthesis and the development of new pharmaceuticals.
Used in Organosilicon Chemistry:
1-BOC-5-METHOXYINDOLE is used as a reactant in the synthesis of 2-(indolyl) borates, silanes, and silanols, which are important intermediates in organosilicon chemistry and have potential applications in materials science and surface modification.
Used in Anticancer Drug Development:
1-BOC-5-METHOXYINDOLE is used as a reactant for the preparation of DNA minor groove alkylating agents as stable amine-based prodrugs designed for tumor-specific release. These prodrugs have potential applications in targeted cancer therapy.

InChI:InChI=1/C14H17NO3/c1-14(2,3)18-13(16)15-8-7-10-9-11(17-4)5-6-12(10)15/h5-9H,1-4H3

Upstream product

• 1006-94-6 5-methoxylindole 
• 13303-10-1 tert-Butyl 4-nitrophenyl carbonate 
• 138344-11-3 2-Hydroxy-5-methoxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 157496-75-8 tert-butyl (2-iodo-4-methoxyphenyl)carbamate 
• 129822-42-0 N-(tert-butoxycarbonyl)-4-methoxy-2-methylaniline 
• 102-50-1 2-methyl-4-methoxyaniline 
• 110-62-3 pentanal 
• 192189-10-9 3-iodo-5-methoxyindole-1-carboxylic acid tert-butyl ester 
• 100-52-7 benzaldehyde 
• 75-07-0 acetaldehyde 
• 930-29-0 1-chlorocyclopent-1-ene 
• 290331-71-4 1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid 

Downstream Products

• 290331-71-4 1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid 
• 1256359-99-5 tert-butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole-1-carboxylate 
• 1428884-68-7 potassium (1-((tert-butoxy)carbonyl)-5-methoxy-1H-indol-2-yl)trifluoroboranuide 
• 10371-86-5 9-methoxyellipticine 
• 906779-78-0 2-(3-chlorophenyl)-5-methoxy-1H-indole 
• 7699-18-5 5-methoxyindolin-2-one 
• 290331-87-2 5-Methoxy-1-methyl-2-(3-methyl-2-pyridyl)-1H-indole-3-carbaldehyde 

Relevant articles and documents

An entry to 2-(cyclobut-1-en-1-yl)-1: H -indoles through a cyclobutenylation/deprotection cascade

A transition-metal-free strategy for the synthesis of 2-(cyclobut-1-en-1-yl)-1H-indoles under mild conditions is described herein. A series of substituted 2-(cyclobut-1-en-1-yl)-1H-indoles are accessed by a one-pot cyclobutenylation/deprotection cascade from N-Boc protected indoles. Preliminary experimental and density functional theory calculations suggest that a Boc-group transfer is involved in the underlying mechanism.

Diastereodivergent Intermolecular 1,2-Diamination of Unactivated Alkenes Enabled by Iodine Catalysis

The stereospecific, substrate (nitrogen source)-controlled intermolecular anti-and syn-1,2-diaminations of unactivated alkenes using the same catalysis (an iodine catalyst) is reported. The combined use of the two potential methods provides access to all of the disastereomeric forms of 1,2-diamines in spite of the availability of E-and Z-Alkenes, and the resulting products can be readily converted into free vicinal diamines.

Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes

A new method for the synthesis of bi-heteroaryls is reported, based on the umpolung of indoles with benziodoxol(on)e hypervalent iodine reagents (IndoleBX). The oxidative coupling of IndoleBX with an equimolar amount of electron-rich benzenes, indoles, pyrroles, and thiophenes proceeded under mild transition-metal-free conditions. Functionalized non-symmetrical bi-indolyl heterocycles were accessed efficiently. Introduction of a new type of C2-substituted indole benziodoxole reagents further allowed extending the scope of the reaction to NH unprotected and C3-alkylated indoles. The obtained bi-heterocycles are important building blocks in synthetic and medicinal chemistry, and could be easily transformed into more complex heterocyclic systems.

Direct C-H Cyanation of Arenes via Organic Photoredox Catalysis

Methods for the direct C-H functionalization of aromatic compounds are in demand for a variety of applications, including the synthesis of agrochemicals, pharmaceuticals, and materials. Herein, we disclose the construction of aromatic nitriles via direct C-H functionalization using an acridinium photoredox catalyst and trimethylsilyl cyanide under an aerobic atmosphere. The reaction proceeds at room temperature under mild conditions and has proven to be compatible with a variety of electron-donating and -withdrawing groups, halogens, and nitrogen- and oxygen-containing heterocycles, as well as aromatic-containing pharmaceutical agents.

Synthesis and antitumor activity of new thiazole nortopsentin analogs

New thiazole nortopsentin analogs in which one of the two indole units was replaced by a naphthyl and/or 7-azaindolyl portion, were conveniently synthesized. Among these, three derivatives showed good antiproliferative activity, in particular against MCF7 cell line, with GI50 values in the micromolar range. Their cytotoxic effect on MCF7 cells was further investigated in order to elucidate their mode of action. Results showed that the three compounds act as pro-apoptotic agents inducing a clear shift of viable cells towards early apoptosis, while not exerting necrotic effects. They also caused cell cycle perturbation with significant decrease in the percentage of cells in the G0/G1 and S phases, accompanied by a concomitant percentage increase of cells in the G2/M phase, and appearance of a subG1-cell population.

Synthesis and antiproliferative activity of thiazolyl-bis-pyrrolo[2,3-b]pyridines and indolyl-thiazolyl-pyrrolo[2,3-c]pyridines, nortopsentin analogues

Two new series of nortopsentin analogues, in which the imidazole ring of the natural product was replaced by thiazole and indole units were both substituted by 7-azaindole moieties or one indole unit was replaced by a 6-azaindole portion, were efficiently synthesized. Compounds belonging to both series inhibited the growth of HCT-116 colorectal cancer cells at low micromolar concentrations, whereas they did not affect the viability of normal-like intestinal cells. A compound of the former series induced apoptosis, evident as externalization of plasma membrane phosphatidylserine (PS), and changes of mitochondrial trans-membrane potential, while blocking the cell cycle in G2/M phase. In contrast, a derivative of the latter series elicited distinct responses in accordance with the dose. Thus, low concentrations (GI30) induced morphological changes characteristic of autophagic death with massive formation of cytoplasmic acid vacuoles without apparent loss of nuclear material, and with arrest of cell cycle at the G1 phase, whereas higher concentrations (GI70) induced apoptosis with arrest of cell cycle at the G1 phase.

Synthesis and antiproliferative activity of substituted 3[2-(1h-indol-3-yl)- 1,3-thiazol-4-yl]-1h-pyrrolo[3,2-b]pyridines, marine alkaloid nortopsentin analogues

A large number of indolyl-4-azaindolyl thiazoles, nortopsentin analogues, were conveniently synthesized. The antiproliferative activity of the new derivatives was examined against four human tumor cell lines with different histologic origin. Seven derivatives consistently reduced the growth of the experimental models independently of TP53 gene status and exhibited the highest activity against the malignant peritoneal mesothelioma (STO) cell line. The most active compound of this series acts as a CDK1 inhibitor, and was found to cause cell cycle arrest at G2/M phase, to induce apoptosis by preventing the phosphorylation of survivin in Thr34 and to increase the cytotoxic activity of paclitaxel in STO cells.

Novel 1H-pyrrolo[2,3-b]pyridine derivative nortopsentin analogues: Synthesis and antitumor activity in peritoneal mesothelioma experimental models

In this study, we describe the synthesis of new nortopsentin analogues, 1H-pyrrolo[2,3-b]pyridine derivatives and their biological effects in experimental models of diffuse malignant peritoneal mesothelioma (DMPM), a rare and rapidly fatal disease, poorly responsive to conventional therapies. The three most active compounds, 1f (3-[2-(5-fluoro-1-methyl-1H-indol-3-yl)-1,3- thiazol-4-yl]-1H-pyrrolo[2,3-b]pyridine), 3f (3-[2-(1H-indol-3-yl)-1,3-thiazol- 4-yl]-1-methyl-1H-pyrrolo[2,3-b]pyridine), and 1l (3-[2-(5-fluoro-1-methyl-1H- indol-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrolo[2,3-b] pyridine), which were shown to act as cyclin-dependent kinase 1 inhibitors, consistently reduced DMPM cell proliferation and induced a caspase-dependent apoptotic response, with a concomitant reduction of the expression of the active Thr34- phosphorylated form of the antiapoptotic protein survivin. Moreover, the combined treatment of DMPM cells with 3f derivative and paclitaxel produced a synergistic cytotoxic effect, which was paralleled by an enhanced apoptotic response. In the mouse model, i.p. administration of 1f, 3f, and 1l derivatives was effective, resulting in a significant tumor volume inhibition of DMPM xenografts (range, 58-75%) at well-tolerated doses, and two complete responses were observed in each treatment group.

A trans diacyloxylation of indoles

A trans diacyloxylation of indoles is accomplished by employing PhI(OAc)2 as the oxidant. A broad range of functional groups are well tolerated. Both the electronic properties of the N-protecting groups of indoles and the acidity of the reaction media play important roles in the selectivity of indole acyloxylation reactions. The Royal Society of Chemistry 2012.

Suzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides

A protocol for the Suzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides that minimizes protodeboronation is described. A combination of catalytic amounts of Pd(OAc)2 and SPhos in conjunction with CsF in isopropanol effectivel