4072-67-7

Usage

Uses

Used in Organic Synthesis:
4,4'-Bis(2-bromoacetyl)biphenyl is used as a building block for the synthesis of complex organic compounds due to its unique structure and reactivity. Its bromoacetyl groups facilitate various chemical reactions, making it a valuable component in the creation of new molecules with specific properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,4'-Bis(2-bromoacetyl)biphenyl is utilized as a reagent for the synthesis of pharmaceutical compounds. Its ability to participate in organic reactions allows for the development of new drugs with potential therapeutic applications.
Used in Chemical Industries:
4,4'-Bis(2-bromoacetyl)biphenyl is also employed in other chemical industries for the synthesis of specialty chemicals, materials, and intermediates. Its versatility in chemical reactions contributes to the production of a wide range of chemical products.
It is crucial to handle 4,4'-Bis(2-bromoacetyl)biphenyl with care, considering its reactive and potentially hazardous nature. Proper safety measures should be taken during its use to minimize risks associated with this chemical compound.

Upstream product

• 92-52-4 biphenyl 
• 598-21-0 2-Bromoacetyl bromide 
• 99-90-1 para-bromoacetophenone 
• 99-73-0 para-bromophenacyl bromide 
• 98-80-6 phenylboronic acid 
• 787-69-9 4,4'-diacetylbiphenyl 

Downstream Products

• 123489-67-8 4,4'-bis(2,3,5,6-tetrahydro-1,4-oxazin-4-ylacetyl)biphenyl dimethiobromide 
• 20275-19-8 4,4'-bis-[(2-methyl-pyridinio)-acetyl]-biphenyl; dibromide 
• 19035-84-8 4,4'-bis-[(4-methyl-pyridinio)-acetyl]-biphenyl; dibromide 
• 122765-43-9 4,4'-bis-{[dimethyl-(2-methyl-[1,3]dioxolan-4-ylmethyl)-ammonio]-acetyl}-biphenyl; dibromide 
• 121446-64-8 4,4'-bis-[(5-ethyl-2-methyl-pyridinio)-acetyl]-biphenyl; dibromide 
• 15172-86-8 4,4'-bis-[(3-methyl-pyridinio)-acetyl]-biphenyl; dibromide 
• 113090-48-5 4,4'-bis-(2-methyl-thiazol-4-yl)-biphenyl 
• 13717-24-3 4,4'-Bis-<-(2,2-diaethoxy-aethyl)-N,N-dimethyl-ammonioacetyl>-biphenyl-dibromid 
• 37750-85-9 4,4'-Bis-[N-methyl-N,N-bis-(2-aethoxy-aethyl)-ammonioacetyl]-biphenyl-dibromid 
• 123489-65-6 4,4'-bis(pyrrolidinoacetyl)biphenyl dihydrobromide 
• 123489-70-3 4,4'-bis(piperidinoacetyl)biphenyl dihydrobromide 
• 123489-64-5 4,4'-bis(pyrrolidinoacetyl)biphenyl dimethiobromide 
• 123489-62-3 4,4'-bis<(2-methylpyrrolidino)acetyl>biphenyl dimethiobromide 
• 123489-63-4 4,4'-bis<(3-methylpyrrolidino)acetyl>biphenyl dimethiobromide 

Relevant academic research and scientific papers

MICRO-ELECTROLYSIS REACTOR FOR ULTRA FAST, OXIDANT FREE, C-C COUPLING REACTION AND SYNTHESIS OF DACLATASVIR ANALOGS THEREOF

The present invention relates to a continuous micro-electro-flow reactor system for ultra-fast, oxidant free, C—C coupling reaction for making symmetrical biaryls and analogs thereof. This invention further relates to the said process for preparation of antiviral drug, daclatasvir of general formula I.

Preparation method for 4,4'-di(2-bromoacetyl) biphenyl

The invention relates to a preparation method for 4,4'-di(2-bromoacetyl) biphenyl. The preparation method comprises the following steps: step (1), enabling bromoacetyl bromide to react with biphenyl in the presence of a chloralkane solvent and a catalyst, thereby obtaining a first mixed system; (2) providing an anti-solvent to react with the first mixed system, thereby obtaining a second mixed system containing 4,4'-di(2-bromoacetyl) biphenyl; (3) treating the second mixed system obtained in step (2), thereby obtaining 4,4'-di(2-bromoacetyl) biphenyl. The method is simple in process, is safe to operate, avoids use of a toxic solvent, and effectively inhibits generation of monosubstituted byproducts, so that the obtained product yield exceeds 80%, and purity is as high as 99.0%, and therefore, the preparation method is a route which can be used for industrial production.

Synthesis method of Daclatasvir

The invention relates to a synthesis method of Daclatasvir. The method comprises the following steps: step 1, performing a bromination reaction on 4.4-diacetyl biphenyl which serves as a raw material so as to obtain an intermediate 1; step 2, performing a substitution reaction on the intermediate 1 so as to obtain an intermediate 2; step 3, performing a cyclization reaction on the intermediate 2 so as to finally obtain the Daclatasvir. Compared with reported synthesis routes, a synthesis route of the method has the following advantages that the route is short, and the yield is high; general means such as suction filtration, extraction and concentration are adopted for aftertreatment, and aftertreatment is simple and convenient; severe-pollution and high-toxicity reagents such as bromine are avoided, and a process of repeatedly using an acetic acid washing reaction system is avoided.

Daclatasvir synthetic method

The invention provides a daclatasvir synthetic method. The method comprises the following steps: taking 4,4'-di(2-halogenated acetyl)biphenyl as a raw material, performing an esterification reaction with N-(methoxycarbonyl)-L-valine-L-proline in an organic solvent under alkali existence to obtain an intermediate B; then performing a dehydrating-cyclizing reaction on the intermediate B and ammonium acetate in an xylene solution at the temperature of 100-120 DEG C to obtain free alkali C; and reacting the free alkali C and HCl to obtain a daclatasvir crude product; and finally re-crystallizing the daclatasvir crude product to obtain daclatasvir. The synthetic method has the advantages of simple synthesis route, convenient operation and simple purifying, the purity of daclatasvir obtained by the synthesis reaction is high, the yield is large, quality of the daclatasvir bulk drug is greatly increased, production cost is reduced, and the method is suitable for large industrial production.

4,4'-bis(2-bromoacetyl) biphenyl synthesizing method

The invention discloses a 4,4'-bis(2-bromoacetyl) biphenyl synthesizing method. The method comprises the following steps of 1, adding methylene dichloride and anhydrous aluminum chloride into a reacting kettle, dropwise adding acetyl chloride after cooling, after finishing adding the acetyl chloride, continuously dropwise adding methylene dichloride solution of biphenyl; 2, warming to carry out friedel-crafts reaction after finishing adding the methylene dichloride solution, adding water after finishing the reaction, concentrating, crystallizing and drying to obtain a product of 4.4-diacetyl biphenyl; 3, adding the 4.4-diacetyl biphenyl into acetic acid and then adding bromine to carry out substitution reaction; 4, filtering, concentrating and crystallizing to obtain the 4,4-bis(2-bromoacetyl) biphenyl after finishing the reaction. By means of the method, the obtained product is higher in both purity and yield.

Facile Suzuki-Miyaura coupling of activated aryl halides using new CpNiBr(NHC) complexes

Nine new Ni(II)-NHC complexes, [CpNiBr(NHC)], were synthesised from nickelocene and the corresponding symmetric or asymmetric alkyl/-benzyl/phenylethyl imidazolium bromide ligands in relatively high yield. Access to each of the synthesised symmetric or asymmetric alkyl/benzyl/phenylethyl imidazolium bromide salts was obtained through deprotonation of imidazole, followed by treatment with an alkyl- or aryl halide, which is subsequently followed with reaction of a secondary alkyl-, benzyl-, or phenylethyl halide. The series of [CpNiBr(NHC)] exhibited catalytic activity in the Suzuki-Miyaura coupling of activated aryl halides with phenylboronic acid to give the respective biphenyl and biphenyl-containing products. In general, the more electron-donating NHC-bearing Ni complexes showed higher activity with aryl halides bearing electron-withdrawing functionalities including carboxaldehyde moieties. All complexes were characterised by 1H and 13C NMR spectroscopy, FT-IR spectroscopy, CHN and MS analyses, along with six selected single crystal X-ray structures that are reported here.

Design and synthesis of imidazole N-H substituted amide prodrugs as inhibitors of hepatitis C virus replication

Abstract Twenty-five novel imidazole N-H substituted Daclatasvir (BMS-790052, DCV) analogues (8a-8y) were designed and synthesized as potential prodrugs. Structure modifications were performed in order to improve potency and pharmacokinetic (PK) properties. All target compounds were evaluated in a hepatitis C virus (HCV) genotype 1b replicon, and the 2-oxoethyl acetate substituted compound 8t showed similar anti-HCV activity (EC50 = 0.08 nM) to that of the lead compound Daclatasvir. Moreover, the utility of prodrug 8t was demonstrated through similar exposure of the parent compound when the prodrugs were dosed in vivo. PK studies showed that prodrug 8t was an ideal candidate for a slower and sustained release form of Daclatasvir.

Design, synthesis and evaluation of novel anti-HCV molecules that deliver intracellularly three highly potent NS5A inhibitors

The design and synthesis of new non-symmetrical NS5A inhibitors with sulfur containing amino acids is reported along with their ability to block HCV replication in an HCV 1b replicon system. These compounds display EC50 values in the picomolar range with a large therapeutic index (>106). Moreover, cellular pharmacology studies show that our preferred compounds intracellularly deliver three potent NS5A inhibitors.

CRYSTALLINE FORM OF METHYL ((1S)-1-(((2S)-2-(5-(4'-(2-((2S)-1-((2S)-2-((METHOXYCARBONYL)AMINO)-3-METHYLBUTANOYL)-2-PYRROLIDINYL)-1H-IMIDAZOL-5-YL)-4-BIPHENYLYL)-1H-IMIDAZOL-2-YL)-1-PYRROLIDINYL)CARBONYL)-2-METHYLPROPYL)CARBAMATE DIHYDROCHLORIDE SALT

The present disclosure generally relates to a crystalline form of methyl ((1S)-1-(((2S)-2-(5-(4'-(2-((2S)-1-((2S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-2-pyrrolidinyl)-1 H-imidazol-5-yl)-4-biphenylyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate dihydrochloride salt. The present disclosure also generally relates to a pharmaceutical composition comprising a crystalline form, as well as methods of using a crystalline form in the treatment of Hepatitis C and methods for obtaining such crystalline form.

18-Crown-6 Catalyzed Microwave-mediated Synthesis of Symmetric Bis-Heterocyclic Compounds under Solvent-free Condition

An efficient, solvent-free and 18-crown-6 catalyzed method for the synthesis of N-alkyl-4-(4-(5-(2-(alkyl-amino)thiazol-4-yl)pyridin-3-yl)phenyl)thiazol-2-amine, N-alkyl-4-(5-(2-alkyamino)thiazol-4-yl)pyridine-3-yl)thiazol-2-amine, and 4,4′-bis-{2-[amino]-4-thiazolyl}biphenyl bis-heterocyclic derivatives via microwave accelerated cyclization is presented.