Category: 143612-79-7

143612-79-7, 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 15 A solution of 10.8 g of 3-[4-(N,N-bis(2-chloroethyl)amino)butyl]-5-cyanoindole (“E”) [obtainable by reaction of 3-(4-chlorobutyl)-5-cyanoindole with N,N-bis(2-chloroethyl)amine] and one equivalent of p-methoxyaniline in 200 ml of acetonitrile is stirred for 12 hours at room temperature and worked up in a conventional manner, and 3-[4-(4-p-methoxyphenylpiperazino)butyl]-5-cyanoindole, m.p. 207 (dec.), is obtained., 143612-79-7

The synthetic route of 143612-79-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck Patent Gesellschaft mit Beschrankter Haftung; US5418237; (1995); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

143612-79-7, 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 3 (233 g, 1.0mol) and 6 (245 g, 1.0 mol) were dissolved in acetonitrile (3 L), and then, triethylamine (101 g, 1.0mol) and K2CO3 (138g,1.0mol) were added to the solution. The mixture was heated at reflux for 12 h. Subsequently, the reaction mixture was poured into cold water (3L). After filtration, the solid was dissolved in EtOAc, and then, HCl-EtOAc saturated solution was added to enable crystallization. Product 7 was obtained as a white solid. Yield 287 g (65%) with 99% HPLC purity after the mixture was filtered. m.p. 276.5-279.2C (Lit1 277-279C). 1H NMR (400MHz, DMSO-d6): delta 11.35 (s, 1H), 8.04 (d, J=18.3Hz, 2H), 7.74-6.88 (m, 8H), 3.69-3.15 (m, 8H), 2.74 (t, J= 7.2Hz, 2H), 2.37 (t, J =7.2Hz, 2H), 1.80-1.61 (m, 2H), 1.54 (d, J=6.8Hz, 2H). 13C NMR (100 MHz, DMSO-d6): delta 159.9, 148.8, 147.9, 138.6, 137.7, 127.8, 126.9, 124.7, 124.0, 123.3, 120.9, 117.8, 115.7, 112.4, 111.6, 109.5, 107.3, 100.0, 57.5, 52.8(2), 49.8(2), 27.7, 26.1, 24.1. HRMS (ESI): m/z [M+H]+ calculated for C26H27N5O2: 442.2238, found: 442.2240.

143612-79-7, As the paragraph descriping shows that 143612-79-7 is playing an increasingly important role.

Reference£º
Article; Hu, Fan; Su, Weike; Journal of Chemical Research; vol. 44; 3-4; (2020); p. 243 – 247;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

143612-79-7, 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The title compound of this step was prepared by the method described in Example 1, Step 3, namely, 5 -(2-(piperazin- 1 -yl)pyrimidin-5 -yl)pyridine-2-carboxamide dihydrochloride (400 mg, 1.12 mmol), 3-(4-chlorobutyl)-1H-indole-5-nitrile (312 mg, 1.34 mmol), anhydrous sodium carbonate (712 mg, 6.72 mmol) and sodium iodide (50 mg, 0.33 mmol) were added to anhydrous acetonitrile (15 mL). The mixture solution was heated to 90 C and reacted for 36 hours. The crude product was separated and purified by column chromatography (dichloromethane/methanol (v/v) = 20/1) to give the title compound as a white solid (390 mg, 73.6%).MS (ESI, pos. ion) m/z: 481.70 [M+H].?H N?1R (600 IVIHz, DMSO-c16) (ppm): 11.36 (s, 1H), 8.92 (s, 1H), 8.83 (s, 2H),8.318.18 (m, 1H), 8.07 (d, J= 10.5 Hz, 3H), 7.63 (s, 1H), 7.50 (d, J 8.4 Hz, 1H), 7.40 (d, J8.4 Hz, 1H), 7.34 (s, 1H), 3.80 (brs, 4H), 2.74 (t, J= 7.3 Hz, 2H), 2.42 (brs, 4H), 2.37 (t, J 7.0Hz, 2H), 1.67 (dd, J= 14.6, 7.4 Hz, 2H), 1.54 (d, J= 6.6 Hz, 2H); HPLC: 99.42%., 143612-79-7

143612-79-7 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile 9881123, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; JIN, Chuanfei; ZHONG, Wenhe; LIANG, Haiping; ZHANG, Yingjun; (79 pag.)WO2019/62662; (2019); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

143612-79-7, 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

under nitrogen protection,A commercially available 6.8 g of 3- (4-chlorobutyl) -5-cyanoindole was dissolved in 70 mL of ether with 8.9 g of cuprous iodide to form a reaction solution,Heated to reflux for 3.5 hours.Then the commercially available 5.9g5-piperazine-benzofuran 2-carboxylate and60 g of sodium methoxide was added to the stirred reaction solution,The reaction solution was reacted at 90 C for 5.5 hours until TLC was complete.The reaction solution was cooled to room temperature and poured slowlyStirring in 100 mL of aqueous potassium hydroxide solution, a large amount of yellow solid precipitated and precipitatedThe solid reaction solution was stirred for 1 hour and then filtered to obtain a filter cake which was washed with 50 mL of waterAfter three runs, 8.9 g of 5- (4- [4- (5-cyano-3-indolyl) -butyl] -1-piperazinyl)Benzofuran-2-carboxylate., 143612-79-7

143612-79-7 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile 9881123, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Suzhou Uugene Biopharma Co., Ltd.; Hu, Fan; Wang, Shenyong; Shao, Changkun; Li, Sheng; Wang, Xiaojun; Hu, Junkai; (12 pag.)CN103360373; (2016); B;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.143612-79-7,3-(4-Chlorobutyl)-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

The title compound of this step is prepared by the method described in the third step of Example 1,4-methyl-2-(2-(piperazin-1-yl)pyrimidin-5-yl)oxazole-5-carboxamide dihydrochloride (500 mg, 1.38 mmol),3-(4-Chlorobutyl)-1H-indole-5-carbonitrile (386 mg, 1.66 mmol), anhydrous sodium carbonate (878 mg, 8.28 mmol)Sodium iodide (63 mg, 0.42 mmol) was prepared in acetonitrile (15 mL) at 90 C for 36 hours.The obtained crude product was further purified by silica gel chromatography (dichloromethane:methanol (V:V)=30:1) to give the title compound(light yellow solid, 492 mg, 73.6%)., 143612-79-7

143612-79-7 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile 9881123, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhong Wenhe; Liang Haiping; Zhang Yingjun; (57 pag.)CN109574993; (2019); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.143612-79-7,3-(4-Chlorobutyl)-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

6-(2-(Piperazin- 1 -yl)pyrimidin-5-yl)nicotinamide dihydrochloride (400 mg, 1.12 mmol), 3-(4-chlorobutyl)-1H-indole-5-nitrile (312 mg, 1.34 mmol), anhydrous sodium carbonate (712 mg, 6.72 mmol) and sodium iodide (50 mg, 0.33 mmol) were added into anhydrous acetonitrile (15 mL) in turn. The solution was heated to 90 C and reacted for 36 hours. The reaction was stopped, and the mixture was cooled to room temperature. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (dichloromethane/methanol (v/v) = 20/1) to give the title compound as a faint yellow solid (465 mg, 86.4%).MS (ESI, pos. ion) m/z: 481.30 [M+H].?H NIVIR (400 1?IFlz, DMSO-d6) (ppm): 11.36 (s, 1H), 9.08 (s, 2H), 9.04 (d, J= 1.7 Hz,1H), 8.26 (dd, J= 8.3, 2.1 Hz, 1H), 8.14 (s, 1H), 8.10 (s, 1H), 8.05 (d, J= 8.3 Hz, 1H), 7.52 (s,1H), 7.49 (d, J= 8.3 Hz, 1H), 7.40 (dd, J= 8.4, 0.9 Hz, 1H), 7.35 (s, 1H), 3.90 (brs, 4H), 3.39(brs, 4H), 2.73 (t, J 7.4 Hz, 2H), 2.452.39 (m, 2H), 1.731.65 (m, 2H), 1.54 (d, J= 6.7 Hz,2H);HPLC: 95.11%.

143612-79-7, 143612-79-7 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile 9881123, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; JIN, Chuanfei; ZHONG, Wenhe; LIANG, Haiping; ZHANG, Yingjun; (79 pag.)WO2019/62662; (2019); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles