Category: nitriles-buliding-blocks

Reference of 179898-34-1, 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.

Under argon, 3.60 g (18.0 mmol) of 3-bromo-5-fluorobenzenecarbonitrile, 5.03 g (19.8 mmol) of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane and 5.30 g (54.0 mmol) of potassium acetate are provided in 72 ml of degassed 1,4-dioxane/DMSO (10/1), and 441 mg (0.54 mmol) of 1,1′-bis(diphenylphosphine)ferrocenedichloropalladium(II)/dichloromethane complex are added. The mixture is stirred at 90 C. overnight. Water is subsequently added, the phases are separated, the aqueous phase is extracted with ethyl acetate and the combined organic phases are concentrated. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1). 4.48 g (92% of theory) of the title compound are obtained.1H-NMR (400 MHz, DMSO-d6): delta=8.01 (ddd, 1H), 7.82 (s, 1H), 7.70 (ddd, 1H), 1.32 (s, 12H).GC-MS (Method 11): Rt=4.94 min; MS (EIpos): m/z=247 [M]+.

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AiCuris GmbH & Co. KG; US2012/22059; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 54454-12-5, name is 3-Chloro-2-methylbenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 54454-12-5, Computed Properties of C8H6ClN

A. 3-Chloro-2-methylbenzaldehyde To 3-chloro-2-methylbenzonitrile (5 g, 33 mmol) in dichloromethane (150 mL) at -78 C. was added DiBAL (1M in dichloromethane, 41 mL). The reaction mixture was stirred at -78 C. for 2 h then quenched with methanol. The mixture was warmed to 0 C and HCl (10%) was added. The ice-water bath was removed and the mixture was stirred at room temperature for 10 min. The two phases were separated and aqueous phase was extracted with dichloromethane. Combined dichloromethane was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (5% ethyl acetate/hexane) gave 3-chloro-2-methylbenzaldehyde (3.5 g, 69%). 1H NMR (300 MHz, CDCl3) delta 2.64 (s, 3H), 7.21-7.26 (m, 1H), 7.50-7.53(m, 1H), 7.63-7.66 (m, 1H), 10.20 (s, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-methylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ALLERGAN, INC.; US2009/239918; (2009); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 610-66-2, name is 2-(2-Nitrophenyl)acetonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 610-66-2, Recommanded Product: 610-66-2

(1) According to a literature (Grob, C.A.; Helv Chim Acta 1961, 44, 1748.), (2-nitrophenyl)acetonitrile was synthesized from 1-chloro-2-nitrobenzene via (+/-)-ethyl cyano(2-nitrophenyl)acetate. Then, (2-nitrophenyl)acetonitrile (3.37 g) was subjected to catalytic hydrogenation in methanol (17 mL) under a normal pressure using 0.15 g of 10% Pd-C (54% wet). The catalyst was removed by filtration and the solvent was evaporated. Diisopropyl ether (20 mL) was added to the resulting concentrated residue and crystals were recovered by filtration to obtain (2-aminophenyl)acetonitrile (2.05 g). FAB (pos.): m/z 133

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-(2-Nitrophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; YAMANOUCHI PHARMACEUTICAL CO. LTD.; EP1367058; (2003); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 179898-34-1, HPLC of Formula: C7H3BrFN

1003751 Step A: 3-fluoro-5-formylbenzonitrile: A solution of 3-bromo-5- fluorobenzonitrile (5.00 g, 25.0 mmol) in dry THF (25 mL) was cooled to 0 C and 2M iPrMgCl (15.0 mE, 30.0 mmol) in TUF was added dropwise over 5 minutes. The mixture was stirred at 0 C for 15 minutes then at ambient temperature for 1 hour. The mixture was cooled to 0 C and dry DMF (5.81 mL, 75.0 mmol) was added. The mixture was stirred for 17 hours during which time the temperature reached ambient temperature after 2 hours. The mixture was added to ice water (150 mE) and Et20 (100 mE). The biphasic mixture was stirred and treated with 6M HC1 to aqueous pH=3. The organic layer was removed and the aqueous layer extracted with Et20 (2X). The combined Et20 fractions were washed with saturated NaC1 and dried over MgSO4/activated carbon. The dried solution was filtered through a Si02 plug eluting with Et20. The filtrate was concentrated to give the title compound as a yellow solid that was dried in vacuum (3.68 g, 99%). ?H NMR (CDCI3) 8 10.0 (s, 1H), 8.00 (s, 1H), 7.81- 7.86 (m, 111), 7.62-7.67 (m, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven Wade; BLAKE, James F.; BRANDHUBER, Barbara J.; JIANG, Yutong; KERCHER, Timothy; WINSKI, Shannon L.; WO2014/78372; (2014); A1;,
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935-02-4, name is 3-Phenylpropiolonitrile, 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: 935-02-4

General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation product.

The synthetic route of 935-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jinfeng; Zhang, Qi; Ji, Xin; Meng, Ling-Guo; Synlett; vol. 30; 9; (2019); p. 1095 – 1099;,
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Application of 101184-73-0, 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. 101184-73-0, name is 2-(4-Bromophenyl)-2-methylpropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-(4-Bromophenyl)-2-methylpropylamine Prepared from alpha,alpha-dimethyl-(4-bromo)phenylacetonitrile (16 g, 0.0676 mol) using the method of description 4 to afford the title compound as the hydrochloride salt (16.87 g, 89%). 1H NMR (CDCI3) delta: 1.23 (6H, s), 2.89 (2H, s), 7.27 (2H, d, J=9 Hz), 7.43 (2H, d, J=9 Hz), 7.77 (3H, br s).

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-(4-Bromophenyl)-2-methylpropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SmithKline Beecham p.l.c.; US6358974; (2002); B1;,
Nitrile – Wikipedia,
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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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1009-35-4

General procedure: A mixture of benzenesulfonamides (1, 1.0 mmol), halogenated nitrobenzene(2, 1.0 mmol) and K2CO3 (1.1 mmol) were dissolved in DMF in a microwave tube. Then, the reaction mixture was irradiated in a microwave apparatus at 140 °C for 12 minutes. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by column chromatography on silica gel to the desired products 3.

The synthetic route of 1009-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Zhi-You; Liu, Min; Mao, Yi-Jun; Chen, Yu-De; Wang, Yan-Ping; Liu, Chong; Tetrahedron Letters; vol. 60; 8; (2019); p. 626 – 629;,
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1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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: 1813-33-8

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

The synthetic route of 1813-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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Electric Literature of 6609-56-9, 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 6609-56-9 as follows.

To a nitromethane (0.1 mL) solution of 4-methoxybenzonitrile (1f) (30 mg, 0.225 mmol) were addedH2O (1.0 mL), DBU (69 mg, 0.436 mmol), copper (I) iodide (9 mg, 0.0451 mmol), cesium (I)carbonate (37 mg, 0.113 mmol) at room temperature. The reaction mixture was heated at 100 °C for2 h and then poured into water (50 mL). The organic layer was separated and the aqueous layer wasextracted with AcOEt. The combined organic layer was dried over MgSO4. The solvent wasremoved under reduced pressure. The residue was purified by preparative TLC on silica gel elutingwith AcOEt-n-hexane (1:1) to give 2-methoxybenzamide (2f)S5 (17 mg, 50percent) as pale yellow powders.mp 123-125 °C,

According to the analysis of related databases, 6609-56-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kuwabara, Jun; Sawada, Yoshiharu; Yoshimatsu, Mitsuhiro; Synlett; vol. 29; 15; (2018); p. 2061 – 2065;,
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Reference of 127946-77-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 127946-77-4 name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A vial was charged with (1 R,2R)-2-(2-(4,4-difluoropiperidin- 1 -yl)-5 -(4-( 1,1 – dioxidothiomorpholino)phenyl)thiazol-4-yl)cyclohexanecarboxylic acid (42.1 mg, 0.078 mmol), 1 -aminocyclopropanecarbonitrile hydrochloride (23.12 mg, 0.195 mmol), DMF (780 tl), DIPEA (68.1 tl, 0.390 mmol), and HATU (37.1 mg, 0.098 mmol). The resulting mixture was stirred at70 C for 7 hours. Reaction mixture was cooled to RT and purified directly by reverse phase preparative HPLC (H20/ MeCN (10-95%), 0.1% TFA, 20 mm) giving 29mg (61.6%) of (1 R,2R)-N-( 1 -Cyanocyclopropyl)-2-(2-(4,4-difluoropiperidin- 1 -yl)-5 -(4-( 1,1 – dioxidothiomorpholino)phenyl)thiazol-4-yl)cyclohexanecarboxamide (Compound 6) as white solid: MS (ES, m/z): 604.3 (M + 1); ?H NMR (400 MHz, CDC13): oe 0.87-0.86 (m, 2 H); 1.43-1.28 (m, 5 H); 1.85-1.50 (m, 5H); 2.19-2.05 (brm, 4 H); 2.58 (td, J= 11.4, 3.1 Hz, 1 H); 2.80 (td, J = 11.3, 3.2 Hz, 1 H); 3.13-3.11 (m, 4 H); 3.62-3.58 (m, 2 H); 3.74-3.69 (m, 2 H); 3.91-3.89 (m, 4 H); 5.83 (s, 1 H); 6.91 (d, J = 8.5 Hz, 2 H); 7.28 (d, J = 8.4 Hz, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn; PAONE, Daniel, V.; LI, Jing; GINNETTI, Anthony; LIM, John; FU, Jianmin; XU, Shimin; WO2015/54038; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts