1392102-38-3

Basic information

• Product Name: (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole
• Synonyms: (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole;(6S)-3,10-Dibromo-6-phenyl-6H-indolo[1,2-c][1,3]benzoxazine;6H-Indolo[1,2-c][1,3]benzoxazine, 3,10-dibromo-6-phenyl-, (6S)-;Elbasvir N-1
• CAS NO: 1392102-38-3
• Molecular Formula: C₂₁H₁₃Br₂NO
• Molecular Weight: 455.14202
• EINECS: 1592732-453-0
• Mol File: 1392102-38-3.mol

Chemical Properties

• Boiling Point: 606.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.68±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole(1392102-38-3)
• EPA Substance Registry System: (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole(1392102-38-3)

Safety Data

• Hazardous Substances Data: 1392102-38-3(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry and Drug Discovery:
(S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole is utilized as a key intermediate or building block in the synthesis of novel pharmaceutical agents. Its unique structure and potential pharmacological properties make it a promising candidate for the development of new drugs targeting various diseases and conditions.
Used in Organic Synthesis and Chemical Research:
In the field of organic synthesis, (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole serves as a valuable compound for exploring new synthetic methodologies. Its complex structure and reactivity can be harnessed to develop innovative approaches in chemical synthesis, potentially leading to more efficient and selective reactions.
Used in Chemical Libraries for High-Throughput Screening:
(S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole can be incorporated into chemical libraries for high-throughput screening in drug discovery. Its unique structural features may contribute to the identification of new bioactive compounds with potential therapeutic applications.
Used in the Development of Bioactive Molecules:
(S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole can be employed as a starting material or a scaffold in the design and synthesis of bioactive molecules with specific biological activities. Its unique structural elements may enable the development of molecules with novel mechanisms of action or improved pharmacokinetic properties.
Used in the Study of Structure-Activity Relationships:
(S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole can be used to investigate structure-activity relationships in medicinal chemistry. By systematically modifying its structure and evaluating the resulting changes in biological activity, researchers can gain insights into the molecular requirements for optimal pharmacological performance.

Upstream product

• 1585969-17-0 (R)-5-bromo-2-(5-bromoindolin-2-yl)phenol 
• 75-91-2 tert.-butylhydroperoxide 
• 1585969-16-9 (6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo-[5,6][1,3]oxazino[3,4-a]indole 
• 589-21-9 (4-bromophenyl)hydrazine 
• 618-31-5 benzylidene dibromide 
• 1246471-94-2 5-bromo-2-(5-bromo-1H-indol-2-yl)phenol 
• 1585969-24-9 (R)-2-(1-amino-2-(2,5-dibromophenyl)ethyl)-5-bromophenol 
• 1585969-22-7 5-bromo-2-(2-(2,5-dibromophenyl)-1-iminoethyl)phenol 
• 1403991-85-4 1-(4-bromo-2-hydroxyphenyl)-2-(2,5-dibromophenyl)ethanone 
• 1403991-82-1 3-bromophenyl 2-(2,5-dibromophenyl)acetate 
• 100-52-7 benzaldehyde 
• 1369594-56-8 3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole 
• 1369594-43-3 C₁₄H₁₂Br₂N₂O 
• 30186-18-6 4'-bromo-2'-hydroxyacetophenone 

Downstream Products

• 1585969-26-1 (2S,2'S)-di-tert-butyl 2,2'-(5,5'-((S)-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole-3,10-diyl)bis(1H-imidazole-5,2-diyl))bis(pyrrolidine-1-carboxylate) 4-nitrobenzoic acid 
• 1585969-27-2 6-phenyl-3,10-bis(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)-6H-benzo[5,6][1,3]oxazino[3,4-a]indole 
• 1370468-36-2 N,N'-[[(6S)-6-phenyl-6H-indolo[1,2-c][1,3]benzoxazine-3,10-diyl]bis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl-[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]bis[carbamic acid] C,C'-dimethyl ester 

Relevant articles and documents

Facile Quantum Yield Determination via NMR Actinometry

A simplified approach to quantum yield (φ) measurement using in situ LED NMR spectroscopy has been developed. The utility and performance of NMR actinometry has been demonstrated for the well-known chemical actinometers potassium ferrioxalate and o-nitrobenzaldehyde. A novel NMR-friendly actinometer, 2,4-dinitrobenzaldehyde, has been introduced for both 365 and 440 nm wavelengths. The method has been utilized successfully to measure the quantum yield of several recently published photochemical reactions.

Erratum: Facile quantum yield determination via NMR actinometry (Organic Letters (2018) 20:8 (2156-2159) DOI: 10.1021/acs.orglett.8b00391)

On page S22 of the Supporting Information, the path length for the LED NMR system (0.11 cm) was mixed up with the path length of the cuvette for the UV spectrophotometry (1 cm). The path length (I) was incorrectly reported as 0.11 cm. The correct value is

Multi-substituted BODIPY organic photocatalyst catalytic indole oxazolines oxidative dehydrogenation synthesis of indole compounds method

The invention discloses a method for catalyzing synthesis of an indole compound by oxidative dehydrogenation of an indoline compound through a polysubstituted BODIPY organic photocatalyst. The method is characterized in that air or oxygen is taken as an oxidizing agent instead of peroxide, and a polysubstituted BODIPY organic compound serving as a non-metal photocatalyst is used in a reaction. The method has the advantages of small using amount of the catalyst, high catalytic efficiency, mild reaction conditions, easiness in operation environmental friendliness, high product conversion rate and high selectivity, and can be applied to synthesis of nuclear molecules of medicine elbasvir for treating hepatitis C viruses.

A Mild Cu(I)-Catalyzed Oxidative Aromatization of Indolines to Indoles

A novel method for the oxidation of indolines to indoles is described. The method uses a Cu(I) catalyst and an organic percarbonate as the stoichiometric oxidant. The procedure was successfully applied at 0.5 kg scale in the production of a key intermediate in the synthesis of Elbasvir, which is a novel therapy for the treatment of hepatitis C virus infection.

Matched and mixed cap derivatives in the tetracyclic indole class of HCV NS5A inhibitors

A matched and mixed capping SAR study was conducted on the tetracyclic indole class of HCV NS5A inhibitors to examine the influence of modifications of this region on the overall HCV virologic resistance profiles.

PROCESS FOR PREPARING TETRACYCLIC HETEROCYCLE COMPOUNDS

The present invention is directed to a process for preparing Tetracyclic Heterocycle Compounds of formula (I): which are useful as HCV NS5A inhibitors. The present invention is also directed to compounds that are useful as synthetic intermediates for making the compounds of formula (I).

Asymmetric synthesis of cyclic indole aminals via 1,3-stereoinduction

A general and efficient asymmetric synthesis of cyclic indoline aminals was developed with a high level of 1,3-stereoinduction through a dynamic crystallization-driven condensation. Dehydrogenation of the indoline aminals with potassium permanganate produced the corresponding cyclic indole aminals in high yields and excellent enantioselectivities. This general methodology was successfully applied to the synthesis of a wide variety of chiral cyclic indoline aminals and indole aminals with aromatic and aliphatic functional groups.

Enantioselective synthesis of an HCV NS5a antagonist

A concise, enantioselective synthesis of the HCV NS5a inhibitor MK-8742 (1) is reported. The features of the synthesis include a highly enantioselective transfer hydrogenation of an NH imine and a dynamic diastereoselective transformation. The synthesis of this complex target requires simple starting materials and nine linear steps for completion.

TETRACYCLIC INDOLE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION

Tetracyclic indole derivatives of formula (I), pharmaceutically acceptable salts and the pharmaceutical compositions thereof are provided, wherein A, A', G, R1, R15, U, V, V, W, W, X, X', Y, Y' are as defined in the invention. Use of these derivatives for treating hepatitis C virus (HCV) infection is also provided.