129822-49-7

Basic information

• Product Name: 1-(TERT-BUTOXYCARBONYL)-5-METHYLINDOLE&
• Synonyms: tert-Butyl 5-Methyl-1H-indole-1-carboxylate;tert-Butyl 5-methylindole-1-carboxylate
• CAS NO: 129822-49-7
• Molecular Formula: C₁₄H₁₇NO₂
• Molecular Weight: 231.29
• Product Categories: Indoles;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks
• Mol File: 129822-49-7.mol

Chemical Properties

• Boiling Point: 208-209 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.056 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000106mmHg at 25°C
• Refractive Index: n20/D 1.5410(lit.)
• CAS DataBase Reference: 1-(TERT-BUTOXYCARBONYL)-5-METHYLINDOLE&(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(TERT-BUTOXYCARBONYL)-5-METHYLINDOLE&(129822-49-7)
• EPA Substance Registry System: 1-(TERT-BUTOXYCARBONYL)-5-METHYLINDOLE&(129822-49-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 129822-49-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(TERT-BUTOXYCARBONYL)-5-METHYLINDOLE& is used as a reactant for the stereoselective preparation of substituted dihydroindole derivatives via palladium-catalyzed stereoselective carboaminoxylation reactions. This application is crucial for the development of new pharmaceutical compounds with specific biological activities and potential therapeutic benefits.
Used in Chemical Synthesis:
1-(TERT-BUTOXYCARBONYL)-5-METHYLINDOLE& is used as a reactant in the conversion of 1-Boc-indoles to 1-Boc-oxindoles. This transformation is essential for the synthesis of various organic compounds with different functional groups and properties.
Used in Chiral Compounds Synthesis:
In the field of asymmetric synthesis, 1-(TERT-BUTOXYCARBONYL)-5-METHYLINDOLE& is used as a reactant in the preparation of indolyl aromatic chiral alpha-sulfoxides. These chiral compounds are important for the development of enantiomerically pure drugs and other chiral molecules with specific biological activities.
Used in Organometallic Chemistry:
1-(TERT-BUTOXYCARBONYL)-5-METHYLINDOLE& is also used as a reactant in the preparation of (indolyl)borates, silanes, and silanols. These organometallic compounds have a wide range of applications in organic synthesis, including the formation of carbon-carbon and carbon-heteroatom bonds, as well as the development of new catalysts and reagents for various chemical transformations.

InChI:InChI=1/C14H17NO2/c1-10-5-6-12-11(9-10)7-8-15(12)13(16)17-14(2,3)4/h5-9H,1-4H3

Upstream product

• 95-68-1 2,4-Xylidine 
• 129822-43-1 (2,4-dimethylphenyl)carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 614-96-0 5-methyl-1H-indole 
• 138344-33-9 2-Hydroxy-5-methyl-2,3-dihydro-indole-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) 
• 442685-53-2 t-butyl 5-(bromomethyl)-1H-indole-1-carboxylate 
• 475102-18-2 2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester 
• 475102-14-8 {1-[(tert-butoxy)carbonyl]-5-methyl-1H-indol-2-yl}boronic acid 

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.

THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION

Disclosed herein are compounds of formula I: or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I or a pharmaceutically acceptable salt thereof, alone or in combination with a bacterial efflux pump inhibitor.

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.

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 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.

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%).

Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines

Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).