3-(4-Chlorbutyl)-1H-indol-5-carbonitril Basic Product Information

Product Name	3-(4-Chlorbutyl)-1H-indol-5-carbonitril	CAS	143612-79-7
Synonyms	3-(4-Chlorobutyl)indole-5-carbonitrile;3-(4-chlorobutyl)-1H-indole-5-carbonitrile	Molecular Formula	C13H13 Cl N2
EINECS Number	1308068-626-2	Molecular Structure
Appearance	Light Yellow Powder
Purity
Supply Ability

3-(4-Chlorbutyl)-1H-indol-5-carbonitril Quality documents

3-(4-Chlorbutyl)-1H-indol-5-carbonitril Appearance/Package/Shipping/Storage

package

storage condition

Store in cool & dry place,Keep away from strong light and heat

3-(4-Chlorbutyl)-1H-indol-5-carbonitril Application

3-(4-Chlorbutyl)-1H-indol-5-carbonitril literature

Practical and Scalable Manufacturing Process for a Novel Dual-Acting Serotonergic Antidepressant Vilazodone

Jin, Hongshan,Wu, Chengjun,Zhou, Shuhao,Xin, Yunting,Sun, Tiemin,Guo, Chun

, p. 1184 - 1189 (2021)

Vilazodone combines the effects of a selective serotonin reuptake inhibitor with the 5-HT1A receptor partial agonist activity. Here, we report the development of a viable and scalable process for manufacturing vilazodone that features a convergent synthetic approach, with low cost and high purity. The key indole synthesis was improved to first make up the hydrazone intermediate and then modify a pendant hydroxy group to realize a much increased overall yield. This process was successfully used to prepare >2 kg of vilazodone hydrochloride with a total yield of 56.2% and purity of 99.93%.

Allosteric IGF-1R inhibitors

Heinrich, Timo,Graedler, Ulrich,Boettcher, Henning,Blaukat, Andree,Shutes, Adam

, p. 199 - 203 (2010)

Targeting allosteric protein sites is a promising approach to interfere selectively with cellular signaling cascades. We have discovered a novel class of allosteric insulin-like growth factor-I receptor (IGF-1R) inhibitors. 3-Cyano-1H-indole-7-carboxylic acid {1-[4-(5-cyano-1H-indol-3-yl)butyl] piperidin-4-yl}amide (10) was found with nanomolar biochemical, micromolar, cellular IGF-1R activity and no relevant interference with cellular insulin receptor signaling up to 30 ?M. The allosteric binding site was characterized by X-ray crystallographic studies, and the structural information was used to explain the unique mode of action of this new class of inhibitors.

Alternative approach to synthesis of 3-(4-Chloro butyl)- 1H -indole-5-carbonitrile: A key intermediate of vilazodone hydrochloride, an antidepressant drug

Anitha,Reddy, B. Sudhakar,Sekhar,Reddy, K. Venugopal,Chandrasekhar

, p. 3563 - 3571 (2014)

An alternative and efficient telescopic approach to the synthesis of 3-(4-chloro butyl)-1H-indole -5-carbonitrile (2), a key intermediate in the synthesis of vilazodone hydrochloride (1), is described.

Continuous Flow Process for Reductive Deoxygenation of ω-Chloroketone in the Synthesis of Vilazodone

Karadeolian, Avedis,Patel, Dineshkumar,Bodhuri, Prabhudas,Weeratunga, Gamini,Gorin, Boris

, p. 1022 - 1028 (2018)

A continuous flow process for the reductive deoxygenation of 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile to 3-(4-chlorobutyl)-1H-indole-5-carbonitrile was developed using a continuous stirred tank reactor (CSTR) setup. The opportunity for process optimization as well as scale-up feasibility was investigated at a laboratory scale. Advantages of a continuous process such as increased product yield, minimized impurity formation, enhanced safety, and increased overall purity of the isolated material thereby avoiding a purification step were demonstrated. Both sodium borohydride and a borane·THF complex were explored as reducing agents in conjunction with iron trichloride which produced high purity 3-(4-chlorobutyl)-1H-indole-5-carbonitrile not requiring further purification in higher yield than the standard batch process.

Production process 3-(4-chlorobutyl) indole -5- carbonitrile (by machine translation)

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Paragraph 0022; 0025-0036; 0039-0050; 0052-0065, (2020/05/11)

The invention discloses 3 - (4 -chlorobutyl) indo- 5 5-carbonitrile production process, which comprises the following steps, adding :chlorobutyl chloride in a clean reactor: stirring and cooling, with nitrogen in the same reactor at, temperature, and stirring the mixture in a reactor, for one time, to complete dissolution in a solvent, and stirring and cooling by 5 °C, steps: Stirring of 4 - Cooling The reactor, with nitrogen gas in the same reactor at a temperature of about 5-10 °C DEG . The production process of the invention is simple and reliable, production cost, of a reactor in the same reactor is stirred and uniformly: DEG C 5 - and the product purity, is, more suitable for industrialized, large-scale preparation, of the same reactor, and the production process, conditions, are more suitable for industrialized mass preparation of the product in, the same reactor, respectively . (by machine translation)

A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides

Sun, Wanwan,Chen, Xiaobei,Hu, Ying,Geng, Huihui,Jiang, Yuanrui,Zhou, Yuxin,Zhu, Wenjing,Hu, Min,Hu, Haohua,Wang, Xingyi,Wang, Xinli,Zhang, Shilei,Hu, Yanwei

supporting information, (2020/10/05)

A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.

Preparation method of vilazodone intermediate

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Paragraph 0039-0043; 0044-0047, (2020/05/11)

The invention relates to a preparation method of a vilazodone intermediate, which comprises the following steps: carrying out F-C alkylation reaction on a compound 1 raw material and 1-bromo-4-chlorobutane under the action of anhydrous zinc chloride, and carrying out one-step reaction to obtain a compound I, namely, the vilazodone intermediate. Compared with the prior art, the method has the advantages of short reaction route, easiness in post-treatment, high yield, cheap and easily available reagents used in the F-C reaction, convenience in operation, simplicity in post-treatment, low cost, small environmental pollution and suitability for industrial production of the vilazodone intermediate I.

3-(4-Chlorbutyl)-1H-indol-5-carbonitril Upstream and downstream

143612-79-7 Upstream product

• 276863-95-7

  3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile 

• 15861-24-2

  1H-indole-5-carbonitrile 

• 52387-36-7

  6-chlorohexanal 

• 2009-83-8

  6-chloro-1-hexanol 

• 1527470-83-2

  (Z)-4-(2-(6-chlorohexylidene)hydrazinyl)benzonitrile 

• 1527470-88-7

  4-[(2E)-2-(6-chlorohexylidene)hydrazinyl]benzonitrile 

• 873-74-5

  4-Aminobenzonitrile 

• 2863-98-1

  4-hydrazinobenzonitrile hydrochloride 

143612-79-7 Downstream Products

• 143612-66-2

  3-[4-(4-p-methoxyphenylpiperazino)butyl]-5-cyanoindole 

• 163521-11-7

  5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester 

• 163521-12-8

  vilazodone 

• 163521-19-5

  5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}benzofuran-2-carboxylic acid 

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