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Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-(4-Bromophenyl)piperidine is used as a key intermediate in the synthesis of Niraparib (N481400), a novel oral poly(ADP-ribose) polymerase (PARP) inhibitor. (S)-3-(4-Bromophenyl)piperidine is specifically designed to target and inhibit PARP enzymes, which play a significant role in the repair of DNA damage in cancer cells. By inhibiting PARP, Niraparib enhances the DNA repair deficiency in BRCA-1 and -2 mutant tumors, leading to increased cell death and improved treatment outcomes for patients with these specific genetic mutations.

Upstream product

• 6340-79-0 4-oxo-4-(4-bromophenyl)butanoic acid 
• 1284448-67-4 isopropyl 4-(4-bromophenyl)-4-oxobutanoate 
• 1476776-39-2 isopropyl 3-(2-(4-bromophenyl)oxiran-2-yl)-propanoate 
• 1476776-40-5 isopropyl 4-(4-bromophenyl)-5-oxopentanoate 
• 1476776-44-9 (S)-5-(4-bromophenyl)piperidin-2-one 
• 108-86-1 bromobenzene 
• 1008-88-4 3-phenylpyridine 
• 129013-83-8 3-(4-bromophenyl)pyridine 
• 769944-72-1 3-(4-bromo-phenyl)-piperidine 
• 1196713-21-9 (3S)-3-(4-aminophenyl)piperidine 
• 1203683-26-4 (S)-3-(4-bromophenyl)-piperidine hydrochloride 
• 106-37-6 1.4-dibromobenzene 
• 143900-44-1 tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate 
• 232953-62-7 3-[2-(4-bromophenyl)acetyl]-4-isopropyloxazolidin-2-one 

Downstream Products

• 1476776-55-2 (S)-3-(4-bromophenyl)piperidine-1-carboxylic acid tert-butyl ester 
• 1038916-08-3 2-{4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]phenyl}-2H-indazole-7-carboxylic acid 
• 1476776-88-1 C₂₄H₂₇N₃O₄ 
• 1196713-67-3 2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester 
• 1476776-89-2 C₂₅H₂₉N₃O₄ 
• 1038915-73-9 2-[4-((3S)-3-piperidinyl)phenyl]-2H-indazole-7-carboxamide p-toluenesulfonic acid salt 
• 1038915-60-4 (3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine 

Relevant academic research and scientific papers

Niraparib preparation method

The invention provides a niraparib preparation method, which comprises: carrying out photocatalysis on a compound 1 and bromobenzene under a Pd catalyst to obtain a niraparib key intermediate; carrying out chiral resolution on the niraparib key intermediate, and coupling the niraparib key intermediate with NBoc-1H-indazole-7-carboxamide under the catalysis of copper bromide to obtain protected niraparib; and removing the protective color of the protected niraparib under the action of methanesulfonic acid, and obtaining the target product niraparib under tetrahydrofuran pulping. The preparation method of niraparib is simple in synthesis process route, high in preparation efficiency, small in damage to human bodies and the environment and low in synthesis cost.

Preparation method of niraparib intermediate (S)-3-(4-bromophenyl) piperidine

The invention discloses a preparation method of a niraparib intermediate that is (S)-3-(4-bromophenyl) piperidine, which comprises the following steps: by using chiral 1-phenylethylamine as a raw material, carrying out alkylation, condensation, cyclization and reduction, and finally removing an amino protection group to obtain the (S)-3-(4-bromophenyl) piperidine. The preparation method of the (S)-3-(4-bromophenyl) piperidine has the advantages of short route, few steps, simple and convenient process operation, avoidance of use of dangerous reagents, highly toxic reagents and irritant malodorous reagents, reduction of potential safety hazards to operators, reduction of the operation safety level of production, environmental protection, and facilitation of industrialization.

Niraparib intermediate, preparation method and application thereof, and synthesis method of niraparib

The invention relates to a compound alpha-(3-aminopropyl)-p-bromophenylacetic acid, a preparation method and application thereof, (S)-3-(4-bromophenyl)-piperidine-2-one, a preparation method and application thereof, and synthesis methods of (S)-3-(4-bromophenyl)-piperidine) p-toluenesulfonate, N-Boc-(3S)-(4-bromophenyl)piperidine and niraparib. 4-bromophenylacetate 5 is used as a raw material, a nucleophilic reaction is carried out on the raw material and a nitrogen source reagent 4 under the action of an alkali to generate a compound 6; the compound 6 is subjected to deprotection and hydrolysis to obtain an amino acid compound 7; and the amino acid compound 7 is subjected to chiral column separation or chemical resolution to obtain compounds 8 and 9; and the separated enantiomer 8 can besubjected to racemization and resolution conversion (or chiral column separation) to obtain a compound 9, and the process material cost is greatly reduced. After the compound 9 is obtained, a compound1 can be obtained through conventional condensation reaction ring closing, reduction and BOC loading. Splitting operation is advanced, and the enantiomer 8 is subjected to racemization recovery treatment and is repeatedly applied to different splitting batches to continuously obtain the product 9, so the process material cost is lower.

Intermediate for synthesizing niraparib, and preparation method thereof

The invention relates to an intermediate for synthesizing niraparib, and a preparation method thereof, and specifically discloses an intermediate compound I. The compound can be used for preparing a key intermediate (S)-3-(4-bromophenyl)-piperidine for preparing niraparib. The invention also discloses a preparation method of the compound and a preparation method of (S)-3-(4-bromophenyl)-piperidine. The preparation methods provided by the invention do not involve noble metal catalytic reduction or coupling reaction, do not involve enantiomer resolution operation, and have the advantages of lowequipment requirements, low three wastes, short steps, low cost, simplicity in operation and high industrial feasibility.

Preparation method of niraparib intermediate

The invention discloses a preparation method of a niraparib intermediate. The preparation method of the compound represented by formula III is characterized in that a compound represented by formula IV and a compound represented by formula V undergo a sub

Method for industrially producing (S)-3-(4-bromophenyl) piperidine

The invention belongs to the field of chemical medicine synthesis, and provides a method for industrially producing (S)-3-(4-bromophenyl) piperidine. The method comprises the following steps: by taking (S)-1-tert-butyloxycarbonyl-3-hydroxypiperidine as an initial raw material, removing tert-butyloxycarbonyl protecting groups to obtain (S)-3-hydroxypiperidine hydrochloride A; condensing the intermediate A and thionyl chloride to generate a five-membered ring sulfinate intermediate B; oxidizing the intermediate B to generate a five-membered ring sulfonate C; carrying out nucleophilic substitution reaction on the compound C and aryl anions, and meanwhile, carrying out configuration inversion to generate the target product (S)-3-(4-bromophenyl) piperidine. According to the whole process, high-pressure hydrogenation, diazotization and other operations are not used, and no chiral resolution reagent is used, so that the total cost is lower, the operation is simple and convenient, higher chiral purity can be maintained, and the method is suitable for industrial large-scale production.

Method of synthesizing (S)-3-(4-bromophenyl)-piperidine or salt thereof with chiral induction

The invention relates to a method of synthesizing (S)-3-(4-bromophenyl)-piperidine or salt thereof with chiral induction. Particularly, the method comprises the following steps of by taking methyl ortho-4-bromophenylacetate and (S)-(-)-2-methyl-2-propanes

DEUTERATED (S)-2-(4-(PIPERIDIN-3-YL)PHENYL)-2H-INDAZOLE-7-CARBOXAMIDE

A deuterated compound having the structure of Formula I: or a pharmaceutically acceptable salt, solvate, or prodrug thereof; or a salt of a prodrug thereof; or a hydrate or polymorph thereof; whereinY1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y9', Y10, Y10', Y11,

Method for preparing niraparib intermittent S-3-(4-bromophenyl) piperidine

The invention discloses a method for preparing a niraparib intermittent, namely S-3-(4-bromophenyl) piperidine. The method comprises the following steps: (1) performing diazo reaction on S-3-(4-aminophenyl) piperidine and nitrous acid to generate an intermittent compound; (2) enabling the intermittent compound to react with bromide to generate a target product, namely the niraparib intermittent,namely S-3-(4-bromophenyl) piperidine. By adopting the method, S-3-(4-amino phenyl) piperidine is adopted as a raw material, the niraparib intermittent, namely S-3-(4-bromophenyl) piperidine, is synthesized through two steps of diazo reaction and bromination reaction, the process is simplified, the operation is simple to carry out, reaction conditions are gentle, the industrial production difficulties are reduced, in addition, no expensive raw material is used, the production cost can be controlled, and the obtained niraparib intermittent is high in purity and high in yield.

A Niraparib intermediate (S)-3 - (4 - bromophenyl) piperidine preparation method (by machine translation)

The invention discloses a Niraparib intermediate (S)- 3 - (4 - bromophenyl) piperidine of preparation method, the method using the bromo ethyl acetate with N - boc - 3 - amino propyl bromide in alkali under the action of the nucleophilic reaction, ring un