960203-41-2

Usage

Uses

Used in Pharmaceutical Industry:
1-[(2-Bromophenyl)thio]-2,4-dimethylbenzene is used as a chemical intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and medications. Its unique chemical structure allows it to be a key component in the creation of various medicinal compounds.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, 1-[(2-Bromophenyl)thio]-2,4-dimethylbenzene serves as a chemical intermediate, playing a vital role in the production of pesticides, herbicides, and other agricultural chemicals. Its properties make it suitable for enhancing the effectiveness of these products.

Upstream product

• 583-55-1 1-Bromo-2-iodobenzene 
• 13616-82-5 2,4-dimethyl-thiophenol 
• 583-53-9 2,3-dibromobenzene 
• 1541160-62-6 1-((2-bromo)-phenylthio)pyrrolidine-2,5-dione 
• 108-38-3 m-xylene 
• 6320-02-1 o-bromothiophenol 
• 1019453-85-0 2-(2,4-dimethylphenylsulphanyl)benzeneamine 
• 577-19-5 2-nitrophenyl bromide 
• 1610527-49-5 2,4-dimethyl-1-[(2-nitro-phenyl)-sulfanyl]-benzene 
• 94602-20-7 S-(2,4-dimethylphenyl) ethanethioate 
• 4214-28-2 1-iodo-2,4-dimethylbenzene 

Downstream Products

• 960203-42-3 4-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine-1-carboxylic acid tert-butyl ester 
• 508233-74-7 vortioxetine 
• 1293343-18-6 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]-4-methylpiperazine hydrochloride 
• 1293343-20-0 1-[2-(2,4-dimethylphenylsulfanyl)phenyl][1,4]diazepane hydrochloride 
• 31317-18-7 2,4-dimethyldibenzo[b,d]thiophene 
• 960203-27-4 Vortioxetine hydrobromide 
• 960203-28-5 Vortioxetine hydrochloride 
• 960203-37-6 Vortioxetine nitrate 
• 960203-29-6 Vortioxetine mesylate 
• 960203-35-4 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl]piperazine sulfate 
• 960203-36-5 Vortioxetine phosphate 

Relevant academic research and scientific papers

Regioselective C-H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis

A mild and regioselective method for the preparation of unsymmetrical biaryl sulfides using iron(III) catalysis is described. Activation of N-(arylthio)succinimides using the powerful Lewis acid iron(III) triflimide allowed the efficient thiolation of a range of arenes, including anisoles, phenols, acetanilides, and N-heterocycles. The method was applicable for the late-stage thiolation of tyrosine and tryptophan derivatives and was used as the key step for the synthesis of pharmaceutically relevant biaryl sulfur-containing compounds such as the antibiotic dapsone and the antidepressant vortioxetine. Kinetic studies revealed that while N-(arylthio)succinimides bearing electron-deficient arenes underwent thioarylation catalyzed entirely by iron(III) triflimide, N-(arylthio)succinimides with electron-rich arenes displayed an autocatalytic mechanism promoted by the Lewis basic product.

Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis

An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.

Robust Buchwald-Hartwig amination enabled by ball-milling

An operationally simple mechanochemical method for the Pd catalysed Buchwald-Hartwig amination of arylhalides with secondary amines has been developed using a Pd PEPPSI catalyst system. The system is demonstrated on 30 substrates and applied in the context of a target synthesis. Furthermore, the performance of the reaction under aerobic conditions has been probed under traditional solution and mechanochemical conditions, the observations are discussed herein.

Synthesis of Air-stable, Odorless Thiophenol Surrogates via Ni-Catalyzed C?S Cross-Coupling

Thiophenols are versatile synthetic intermediates whose practical appeal is marred by their air sensitivity, toxicity and extreme malodor. Herein we report an efficient catalytic method for the preparation of S-aryl isothiouronium salts, and demonstrate that these air-stable, odorless solids serve as user-friendly sources of thiophenols in synthesis. Diverse isothiouronium salts featuring synthetically useful functionality are readily accessible by nickel-catalyzed C?S cross-coupling of (hetero)aryl iodides and thiourea. Convenient, chromatography-free isolation of these salts is achieved by precipitation, allowing the methodology to be applied directly to large scales. Thiophenols are liberated from the corresponding isothiouronium salts upon treatment with a weak base, enabling an in situ release/S-functionalization strategy that entirely negates the need to isolate, purify or manipulate these noxious reagents.

Preparation method of voltamethine

The invention belongs to the technical field of organic synthesis route design and raw material medicine and intermediate preparation thereof, and particularly relates to a preparation method of voltamethine. The preparation method includes: condensing 2, bromoiodobenzene and 2,4-dimethyl phenylthiophenol to generate a first intermediate; condensing the first intermediate as well as N-phenoxycarbonyl piperazin and tert-butylalcohol to generate a second intermediate; removing a Boc protective group from N-Boc-voltamethine in the second intermediate to generate a crude voltamethine via alkalineionization; purifying the crude voltamethine to obtain the voltamethine via salt purificaton and re-alkalization ionization. The preparation method is simple in obtaining of raw materials, high in product yield and purity and is suitable for industrial production.

PROCESS FOR PREPARATION OF VORTIOXETINE HYDROBROMIDE

The present invention provides a process for preparation of Vortioxetine hydrobromide (I). The present invention also relates to the novel intermediate and its use in preparation of vortioxetine hydrobromide (I).

Synthetic method and application of vortioxetine hydrobromide

The invention relates to the technical field of medicinal chemical synthesis, and concretely relates to a synthetic method of vortioxetine hydrobromide. The method comprises the following steps: carrying out a reaction on compounds comprising o-bromoiodobenzene and 2,4-dimethylthiophenol in environment containing a catalyst, an inorganic alkali and a protic solvent to obtain 2-(2,4-dimethylthiophenyl)bromobenzene; and coupling 2-(2,4-dimethylthiophenyl)bromobenzene with piperazine in environment containing a catalyst, an organic alkali and an aprotic solvent, and carrying out salt formation on the obtained coupling product and hydrobromic acid to prepare the vortioxetine hydrobromide. Compared with the prior art, the method disclosed in the invention has the advantages of solving of double-halogen competition side reactions, great reduction of generation of byproducts, high total yield, good product purity, simplicity in process operation, and suitableness for amplification and industrial production.

Preparation method of vortioxetine hydrobromide

The invention relates to the technical field of preparation of vortioxetine hydrobromide, in particular to a preparation method of vortioxetine hydrobromide. The preparation method comprises the following steps: taking 2,4-dimethyl thiophenol as a raw material to react with o-bromonitrobenzene so as to generate a compound (IV); treating the compound (IV) via a normal pressure catalytic hydrogenation method to obtain a compound (V); treating the compound (V) via a Sandmeyer reaction to obtain a compound (VI); and reacting a compound (VII) with piperazine, and then performing a reaction with hydrobromic acid to generate a salt, thereby obtaining a target compound (I). The method for preparing vortioxetine hydrobromide is relatively short in route, relatively mild in reaction condition, simple, convenient and feasible in after treatment, and more suitable for industrial production requirements.

PROCESS FOR THE PREPARATION OF VORTIOXETINE

Disclosed herein a process for the isolation of intermediate of Vortioxetine in a solid state form and an improved, commercially viable and industrially advantageous process for the preparation of vortioxetine or a pharmaceutically acceptable salt thereof, in high yield and purity.

METHOD FOR MAKING SEROTONIN REUPTAKE INHIBITORS

The present invention relates to a process for preparing serotonin reuptake inhibitors of formula (I) and pharmaceutically acceptable salts thereof, (Formula (I)) wherein, R1, R2, R3, l, m, n and Z are as defined in the sp