129822-46-4

Basic information

• Product Name: N-(BOC)-4-CHLOROINDOLE
• Synonyms: N-(BOC)-4-CHLOROINDOLE;1-BOC-4-Chloroindole;tert-Butyl 4-chloro-1H-indole-1-carboxylate
• CAS NO: 129822-46-4
• Molecular Formula: C₁₃H₁₄ClNO₂
• Molecular Weight: 251.70876
• Mol File: 129822-46-4.mol

Chemical Properties

• Boiling Point: 349.9°C at 760 mmHg
• Flash Point: 165.4°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 4.55E-05mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: Room temperature.
• CAS DataBase Reference: N-(BOC)-4-CHLOROINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(BOC)-4-CHLOROINDOLE(129822-46-4)
• EPA Substance Registry System: N-(BOC)-4-CHLOROINDOLE(129822-46-4)

Safety Data

• Hazardous Substances Data: 129822-46-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
N-(BOC)-4-CHLOROINDOLE is used as a protected amine intermediate for the synthesis of various organic compounds. The BOC protecting group allows chemists to carry out reactions without affecting the amine functionality, which can be selectively removed when needed.
Used in Medicinal Chemistry:
In medicinal chemistry, N-(BOC)-4-CHLOROINDOLE is used as a building block for the development of new pharmaceuticals. The 4-chloroindole moiety can be incorporated into drug candidates to modulate their biological activity, while the BOC group provides a means to control the reactivity of the molecule during synthesis.
Used in Pharmaceutical Research:
N-(BOC)-4-CHLOROINDOLE is utilized in pharmaceutical research as a key intermediate in the synthesis of potential drug candidates. N-(BOC)-4-CHLOROINDOLE's reactivity and the ability to selectively remove the BOC protective group make it a versatile component in the creation of novel therapeutic agents.
Used in the Synthesis of New Chemical Entities:
N-(BOC)-4-CHLOROINDOLE is used as a valuable building block in the synthesis of new chemical entities. The 4-chloroindole structure can influence the physical and biological properties of the compounds it is incorporated into, making it an important component in the development of innovative materials and pharmaceuticals.

InChI:InChI=1/C13H14ClNO2/c1-13(2,3)17-12(16)15-8-7-9-10(14)5-4-6-11(9)15/h4-8H,1-3H3

Upstream product

• 25235-85-2 4-chloro-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4248-19-5 tert-butyl carbazate 
• 1243601-90-2 1-bromo-2-[(E)-2-bromovinyl]-3-chlorobenzene 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 138343-81-4 4-Chloro-2-hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 
• 129822-39-5 N-(tert-butoxycarbonyl)-2-amino-6-chlorotoluene 

Downstream Products

• 1443151-93-6 tert-butyl 4-chloro-2-(4-{[2-(4-fluorophenyl)ethyl]amino}-6-methoxy-1,3,2-triazin-2-yl)-1H-indole-1-carboxylate 
• 1443151-42-5 4-(4-chloro-1H-indol-2-yl)-N-[2-(4-fluorophenyl)ethyl]-6-methoxy-1,3,5-triazin-2-amine 
• 475102-11-5 [1-(tert-butoxycarbonyl)-4-chloro-1H-indol-2-yl]boronic acid 

Relevant articles and documents

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%).

Inherent vs Apparent Chemoselectivity in the Kumada-Corriu Cross-Coupling Reaction

The Kumada-Corriu reaction is a powerful tool for C-C bond formation, but is seldom utilized due to perceived chemoselectivity issues. Herein, we demonstrate that high-yielding couplings can occur in the presence of many electrophilic and heterocyclic functional groups. Our strategy is mechanically based, matching oxidative addition rates with the rate of syringe pump addition of the Grignard reagent. The mechanistic reason for the effectiveness of this strategy is uncovered by continuous-infusion ESI-MS studies.

1,3,5-TRIAZINE-2-AMINE DERIVATIVES, PREPARATION THEREOF AND DIAGNOSTIC AND THERAPEUTIC USE THEREOF

The present invention relates to compounds corresponding to formula (I) in which: - R1 represents a substituted phenyl; - R2 represents: - a substituted phenyl; - a heteroaromatic group, the said group being unsubstituted or substituted one or more times; - R3 represents a group Alk; - R4 represents a hydrogen atom or a (C1-C4)alkyl; - R5 represents a hydrogen atom, a (C3-C6)cycloalkyl or a (C1-C4)alkyl-O-Alk; - or alternatively R4 and R5, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from: azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, morpholin-4-yl; - R6 represents a group -COOAlk, a group -CONH2 or a group -NHSO2 Alk; - Alk represents a (C1-C4)alkyl, which is unsubstituted or substituted one or more times with a halogen atom; in the form of the base or of an acid-addition salt. Preparation process and diagnostic and therapeutic use

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.

Palladium catalyzed tandem alkenyl- and aryl-C-N bond formation: A cascade N-annulation route to 4-, 5-, 6- and 7-chloroindoles

A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared; carbamates, anilines and amines can be employed as the N-nucleophile.

NOVEL P2X7R ANTAGONISTS AND THEIR USE

The present application is directed to novel P2X7R antagonists that are N-indol-3-yl-acetamide and N-azaindol-3-yl-acetamide compounds, pharmaceutical compositions comprising the same and their use for the prophylactic or therapeutic treatment of diseases

2-PHENYL-INDOLES AS PROSTAGLANDIN D2 RECEPTOR ANTAGONISTS

The present invention is directed to 2-phenyl-indole compounds (A), their preparation, pharmaceutical compositions containing these compounds, and their pharmaceutical use in treating a patient suffering from a PGD2-mediated disorder including, but not li

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).