Category: nitriles-buliding-blocks

These common heterocyclic compound, 16532-79-9, name is 4-Bromophenylacetonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 4-Bromophenylacetonitrile

To a solution of 5 g (0.025 mol)Of 4-bromobenzeneacetonitrile were added separately 6 · 47g (0.025mol)The iodine simple substance and40 ml of double distilled tetrahydrofuran,The reaction was dissolved and then cooled to _78 C, Slowly dropping the new system of 52ml of 2.4M sodium methoxide in methanol,Dropping to room temperature after the reaction 10h,Add distilled water to terminate the reaction;With 1M hydrochloric acid to neutral,Extraction with dichloromethane,Washed with saturated saline three times,Drying over anhydrous magnesium sulfate, filtration, rotary evaporation and column chromatography gave 3,4-bis (4-bromophenyl) maleimide in 78% yield.

The synthetic route of 4-Bromophenylacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujian Normal University; Lin Zhenghuan; Ling Qidan; Wang Jingwei; Zheng Rong; Chen Huan; (12 pag.)CN107522646; (2017); A;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 26391-06-0, name is 2-Cyano-N,N-diethylacetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H12N2O

To a mixture of tert-butyl 7-formyl-3,4-dihydroisoquinoline-2(lH)-carboxylate (1 g, 3.83 mmol), 2-cyano-N,N-diethylacetamide (536 mg, 3.83 mmol) and ammonium acetate (1.47 g, 19.13 mmol) in methanol (10 mL) was stirred at reflux for 2 h. After cooling to rt, the mixture was concentrated to dryness. The residue was diluted with EtOAc (40 mL), washed with water (40 mL), followed by brine (40 mL). The organic layer was dried over Na2S04 and concentrated. The crude residue was purified by silica gel chromatography to afford 800 mg of tert-butyl 7-(2-cyano-3-(diethylamino)-3-oxoprop-l-en-l- yl)-3,4-dihydroisoquinoline-2(lH)-carboxylate as a yellow gum.

The synthetic route of 26391-06-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; LOU, Yan; OWENS, Timothy Duncan; BRAMELD, Kenneth Albert; GOLDSTEIN, David Michael; (171 pag.)WO2019/99576; (2019); A1;,
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These common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 3-Bromo-5-fluorobenzonitrile

Step 1 [0668] A solution of 3-bromo-5-fluorobenzonitrile (LXVI) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20C. Then it was stirred at 80C for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20C. The mixture was stirred at 80C for 1 h, then it was washed with EtOAc (300 mL). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL x 3). The combined organic layers were dried over anhydrous Na2SC>4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (LXVII) (24.0 g, 117.62 mmol, 53.5% yield). NMR (CDC13, 300 MHz) ppm 3.86 (s, 2H), 7.01 (d, J=8Hz, IH), 7.12 (d, J=8Hz, IH), 7.28 (s, IH); ESIMS found C7H7BrFN mlz 203.9 (Br79M+H).

The synthetic route of 3-Bromo-5-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23980; (2017); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 39581-21-0, name is N-Butyl-2-cyano-acetamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H12N2O

General procedure: A mixture of N-alkyl-2-cyano-acetamides 1a-c (2 mmol), aldehydes 2a-f (2 mmol),malononitrile (3) (2 mmol), K2CO3 (2 mmol), and EtOH (2 mL) in a 10 mL septum-capped microwavevials was irradiated under microwave conditions at 90 C, 500 W, 200 rpm, for 10-15 min. Aftercompletion of the reaction, as indicated by TLC, each vial was de-capped and the contents were left tocool to room temperature. Then, the reaction mixture was worked up as described in method I to givecompounds 4a-q. Analytical samples were obtained by recrystallization from MeOH.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Mekheimer, Ramadan Ahmed; Al-Sheikh, Mariam Abdullah; Medrasi, Hanadi Yousef; Alsofyani, Najla Hosain Hassan; Molecules; vol. 23; 3; (2018);,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H6BrNO

General procedure: A mixture of ethyl 3-oxo-3-phenylpropanoate (2a) (1.73 mL,10.00 mmol) and allylamine [(3.75 mL, 50.00 mmol) neutralized with acetic acid (2.86 mL, 50.00 mmol)] in ethanol (10 mL) was heated to reflux for 3 h. The resulting mixture was concentrated and the residue was taken up in CH2Cl2. The organic layer was washed with 5% HCl and water, dried over MgSO4 and concentrated. Purification of the crude product by flash column chromatography (silica gel; petroleum ether/ethyl acetate95:5) afforded 3a (2.08 g, 9.00 mmol) in 90% yield as a colourless liquid. When treated with 2c, it afforded 3c instead of 3-(allylamino)-3-(2-fluorophenyl) acrylonitrile.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhai, Sheng-Xian; Dong, Hong-Ru; Chen, Zi-Bao; Hu, Yi-Ming; Dong, Heng-Shan; Tetrahedron; vol. 70; 44; (2014); p. 8405 – 8412;,
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19472-74-3, name is 2-Bromophenylacetonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H6BrN

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60-90 C)-EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60-90C)-EtOAc, 10:1 to 30:1] to give 3ag; Yield: 50.8 mg (99%); fluorescent yellow solid; mp 199.4-201.1 C.

The synthetic route of 19472-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
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51632-29-2, name is 2-(3-Phenoxyphenyl)acetonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 51632-29-2

3-phenoxyphenylacetonitrile was added to a 25 ml Schlenk reaction tube under a nitrogen atmosphere.(0.4 mmol), deuterated dimethylamine borane complex (4 equivalents), potassium t-butoxide (2.5 equivalents), deuterated N,N-dimethylformamide (5 ml), added to the reaction tube After the rubber stopper was placed in an oil bath, the reaction was carried out at 100 C for 18 h, and the end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. The eluent was petroleum ether/acetic acid B. Ester (v:v=10:1),Obtaining alpha-tridemethyl-3-phenoxybenzenepropionitrile;Then, under a nitrogen atmosphere, a 25-ml two-neck round bottom flask was charged with alpha-tridemethyl-3-phenoxyphenylpropionitrile (0.2 mmol), sodium hydroxide (1.5 mmol/ml), water (8 ml). Ethanol (2ml) in round bottomThe flask was placed in a rubber bath and placed in an oil bath. The reaction was refluxed at 110 C for 5 h. The end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. Petroleum ether / ethyl acetate (v: v = 5: 1) gave alpha-tridemethyl-3-phenoxyphenylpropionic acid, alpha-tridemethyl-fenofol.Product yield 70%, light yellow solid

The synthetic route of 51632-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Science and Technology of China; Wang Yifeng; Xia Huimin; Zhang Fenglian; (10 pag.)CN108003004; (2018); A;,
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Electric Literature of 57381-37-0, The chemical industry reduces the impact on the environment during synthesis 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: S3 (1.5 mmol) was dissolved in NEt3 (5 mL) and degassed for 30 minutes at room temperature. Then PdCl2(PPh3)2 (0.2 mol%), CuI (0.2 mol%) and the alkyne were added to S3/NEt3 solution. The obtained dark brown suspension was stirred for 12 h at 60C. After cooling to room temperature the solvent of the reaction mixture was filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography (petroleum ether : ethyl acetate = 30:1) to provide 1t-1w (in 76-83% yield).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromo-5-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
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Application of 3215-64-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3215-64-3 as follows.

Step 22-Cyano-(2,6-dichlorophenyl)-acetic acid methyl ester: A 500 mL round-bottom flask was charged with absolute methanol (100 mL) and sodium (6.2 g, 269.57 mmol). After all of sodium was dissolved, the mixture was evaporated to dryness. Then, 30 mL tolune was added and the mixture was dried down again by evaperation to give fresh NaOMe. To this was added dimethyl carbonate (300 mL) and 2-(2,6- dichlorophenyl)acetonitrile (25 g, 134.41 mmol). The resulting solution was allowed to reflux for 2 hours. The reaction progress was monitored by TLC (AcOEt: PE=I :4). The mixture was quenched by the addition of of 100 mL ice H2O. Then, the pH was adjusted to ca. 6 by the addition of AcOH . The resulting mixture was then extracted with EtOAc (3 x 100 ml). Combined organic layers were then concentrated down in vacuo to afford a residue that was purified by a column chromatography eluted with a 20:1 PE / AcOEt. This resulted in 27.8 g (85%) of methyl 2-cyano-2-(2,6-dichlorophenyl)acetate as a white solid. This was used for next step without further purification.

According to the analysis of related databases, 3215-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KALYPSYS, INC.; WO2007/15866; (2007); A2;,
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Some common heterocyclic compound, 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, molecular formula is C4H7ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C4H7ClN2

A mixture of 2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxylic acid, (EXAMPLE 149), (0.070 g, 0.188 mmol), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (0.147 g, 0.282 mmol), diisopropylethylamine (0.049 ml, 0.282 mmol), and 1-amino-1-cyclopropanecarbonitrile hydrochloride (0.033 g, 0.282 mmol) in DCM (5 mL) was stirred at room temperature for 12 hours. Purification of the reaction mixture using silica chromatography with ISCO eluting with 0-80% EtOAc/hexanes gave the title compound N-(1-cyanocyclopropyl)-2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxamide (0.060 g, 0.137 mmol, 73.1% yield). m/z: 437 (M+1); 1H NMR (400 MHz, DMSO-d6) delta: ppm 8.78 (s, 1H) 8.32 (d, J=6.65 Hz, 1H) 7.93-8.05 (m, 2H) 7.40 (s, 1H) 5.18 (quin, J=8.51 Hz, 1H) 4.31-4.53 (m, 1H) 3.21-3.41 (m, 2H) 2.88-3.05 (m, 1H) 2.29-2.44 (m, 2H) 1.44-1.60 (m, 2H) 1.23-1.35 (m, 2H) 0.93-1.10 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127946-77-4, its application will become more common.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
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