Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, 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 57381-49-4, Quality Control of 2-Bromo-4-chlorobenzonitrile

Borane tetrahydrofuran complex (55 mL, 1.0 M in THF) were provided with ice cooling, then slowly a solution of 2-bromo-4-chlorobenzonitrile (4.00 g, 18.5 mmol) in THF (10 mL) was added. Thereafter the reaction-mixture was heated under reflux for 16 hours. The reaction was quenched by addition of methanol. 20 mL of hydrochloric acid (1.0 N) were added dropwise with ice cooling. The solution was rendered alkaline with 1.0 M sodium hydroxide solution and extracted with dichloromethane. The organic phase was dried over sodium sulfate and evaporated to yield 2.10 g (36%) of the title compound as the off-white solid. The reaction was monitored by TLC (ethyl acetate/petroleum ether=1 :1, Rf = 0.3). MS (ESIpos): m/z = 220 [M+H]+.

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; BAYER PHARMA AKTIENGESELLSCHAFT; WORTMANN, Lars; SAUTIER, Brice; EIS, Knut; BRIEM, Hans; BOeHNKE, Niels; VON NUSSBAUM, Franz; HILLIG, Roman; BADER, Benjamin; SCHROeDER, Jens; PETERSEN, Kirstin; LIENAU, Philip; WENGNER, Antje, Margret; MOOSMAYER, Dieter; WANG, Qiuwen; SCHICK, Hans; (510 pag.)WO2018/172250; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 154607-01-9, A common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

To a 50 mL round bottom flask was added BH3-THF (1.0 M in THF, 32.5 mL, 32.5 mmol) and 4-bromo-2-chlorobenzonitrile (1.76 g, 8.13 mmol) in THF (10 mL). The mixture was heated to reflux for 2 hours. The reaction mixture was quenched by the addition of an aqueous HCl solution (10 wt % yield). The pH was adjusted to 8 by adding an aqueous solution of NaOH (5 wt % yield) and extracted with dichloromethane. The organic layer was dried, filtered and concentrated to afford (4-bromo-2-chloro-phenyl)methanamine (1.62 g, 90% yield), which was used in the next step without further purification. LCMS (ESI) [M+H]+=220.0

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:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 120315-65-3, 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. 120315-65-3, name is 4-Bromo-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 0.17 mmol lnt2.1 in 1.33 mL NMP was combined with 0.44 mmol 4-Bromo-3-methoxybenzonitrile (48.6 mg, 2.6 eq), 0.04 mmol Pd2(dba)3 (36.6 mg, 0.23 eq), 0.12 mmol rac-BINAP (74.7 mg, 0.7 eq) and 0.25 mmol NaOtBu (24.03 mg, 1.5 eq) in a sealed vial and heated at 170 C under microwave irradiation for 2 h. After cooling, the solution was filtered and subjected to preparative HPLC to give 4.7 mg of the title compound. UPLC-MS: RT = 1.15 min; m/z (ES+) 400.5 [MH+]; required MW = 399.5.

The synthetic route of 4-Bromo-3-methoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Schering Pharma AG; EP2343297; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 20099-89-2,Some common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, molecular formula is C9H6BrNO, 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.

Step-I: 4-(2-amino-4-hydroxy-7H-pyrrolo [2, 3-d] pyrimidin-6-yl) benzonitrile (XI- 10- I): A mixture of 2, 6-diaminopyrimidin-4-oI ( 1 g, 7.93 mmol) and NaOAc (0.846 g, 10.31 mmol) in water (180 mL) was heated to 100 C for 20 minutes. To this was added a suspension of 4-(2-bromoacetyl) benzonitrile (2.2 gm, 8.73 mmol) [prepared according to procedure mentioned in J.Med. Chem, 201 1 , 54(12), 4042-4056] in MeOH (25 mL) and heated overnight at 100 C. After completion of reaction, the reaction mixture was cooled to 0 C. Resultant solid product was filtered off and dried under reduced pressure to provide title compound Chi-10-Iota (1.2 g, 100%). LCMS: mlz 252 (M+l )+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(2-Bromoacetyl)benzonitrile, its application will become more common.

Reference:
Patent; ADVINUS THERAPEUTICS LIMITED; THAKKAR, Mahesh; KOUL, Summon; BHUNIYA, Debnath; MOOKHTIAR, Kasim; KURHADE, Santosh; MUNOT, Yogesh; WO2013/157022; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 17354-04-0, name is 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 17354-04-0

General procedure: Piperidine (0.03 ml, 5 mol %) was added to a warm solution of the appropriate salicylaldehyde 5 (5 mmol) and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (1.12 g, 5 mmol) in EtOH (10 ml). The resulting solution was refluxed with stirring for 5 h. The mixture was treated with a solution of concentrated H2SO4 (0.55 ml) in EtOH (2 ml) and refluxed with stirring for 2 h. The obtained precipitate was filtered, washed with EtOH (10 ml), hot H2O (40 ml) and finally with EtOH (10 ml), and dried at 100 C.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 17354-04-0.

Reference:
Article; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 20099-89-2, A common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, molecular formula is C9H6BrNO, 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.

Preparation 4; 4-(2-Methylamino-thiazol-4-yl)-benzylamine; 4-(2-Methylamino-thiazol-4-yl)-benzonitrile; Slurry 4-cyanophenacyl bromide (1.12 g, 5 mmol) in absolute ethanol (25 mL). Heat to 40C to dissolve, then add N-methyl-thiourea (0.45 g, 5 mmol) and sodium bicarbonate (0.42 g, 5 mmol), and heat to reflux for 5 h. Cool to room temperature, filter the resulting off-white solid and wash with hexane (10 mL). Partition aqueous/ethanolic filtrate between water/EtOAc (4: 1) and extract aqueous phase with EtOAc (2×25 mL). Dry the combined organic extracts over Na2SO4, concentrate in vacuo and combine with filtered solid from crude reaction mixture to obtain the desired intermediate (1.1 g, 99%) as an off- white solid suitable for use without additional purification. MS (ES+) m/z: 216 (M+H)+.

The synthetic route of 20099-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/28083; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

425379-16-4, name is 2-Bromo-3-fluorobenzonitrile, 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. Recommanded Product: 2-Bromo-3-fluorobenzonitrile

To a solution of 2-bromo-3-fluorobenzonitrile (10.0 g, 50 mmol) in sulfuric acid (22 mL) was added nitric acid (69%, 4.82 mL, 75 mmol) dropwise, maintaining the temperature between 5-10 C. The reaction mixture turned red-orange at the end of the addition. The reaction mixture was allowed to warm up to RT and was stirred for 1 hour. The reaction mixture was then poured onto crushed ice. The products were extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine (50 mL), dried (MgS04), filtered and concentrated under reduced pressure. The residue was suspended in MeOH (50 mL) and the mixture was briefly heated at reflux. After cooling to RT, a pale yellow precipitate was collected by vacuum filtration, washed with a small amount of MeOH and dried in the vacuum oven. The material was recrystallized from MeOH to afford 1 .77 g (14% yield) of the title compound as a yellow powder.1H NMR (500 MHz, DMSO-d6) delta [ppm] 8.77 (dd, J = 2.5, 1 .4 Hz, 1 H), 8.65 (dd, J = 8.3, 2.5 Hz, 1 H).LCMS (Analytical Method A): Rt = 1 .1 1 min, mass ion not observed.

The synthetic route of 425379-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeURLE, Stefan; DAVENPORT, Adam, James; STIMSON, Christopher; CARR, James, Lindsay; BUBERT, Christian, Abingdon; MARLIN, Frederic, Jacques; NAGEL, Jens; SCHMIDT, Nicole; ROTGERI, Andrea; IRLBACHER, Horst; (378 pag.)WO2018/114783; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 2-Bromo-4-fluorobenzonitrile

Example 10 4-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-4-ylethynyl)benzonitrile Dichloro bis(triphenylphosphine) palladium (II) (29.6 mg, 0.0422 mmol), and triethylamine (742 mul, 534 mg, 5.28 mmol) were added to a solution of intermediate 10.2 (150 mg, 1.06 mmol) and 2-bromo-4-fluorobenzonitrile (1.06 g, 5.28 mmol) in 1,4-dioxane (4 mL), and placed in a sealable tube. Nitrogen gas was bubbled in the reaction mixture for 5 min, before the tube was sealed and the reaction mixture was heated at 80 C. for 2 h. After cooling, the brown solution was filtered through Celite and concentrated under vacuo. The residue was purified by chromatography on a SP1 Biotage system, using hexanes and ethyl acetate as eluents to afford the title compound (33 mg, 12%) as a yellow solid (HPLC: 99%, RT: 6.20 min) 1H NMR (DMSO-d6) delta=12.05 (br s, 1H), 8.31 (d, J=5.1 Hz, 1H), 8.13 (dd, J=8.8, 5.5 Hz, 1H), 7.90 (dd, J=9.3, 2.6 Hz, 1H), 7.69 (dd, J=3.3, 2.6 Hz, 1H), 7.59 (td, J=8.4, 2.6 Hz, 1H), 7.27 (d, J=4.8 Hz, 1H), 6.78 (dd, J=3.7, 1.8 Hz, 1H); MS (m/z) 262 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36282-26-5, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; US2011/282056; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 36282-26-5, 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 36282-26-5 as follows.

4-Fluoro-2-(5-(4-methoxybenzyl)-4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrile. 2-Bromo-4-fluorobenzonitrile, tris(dibenzylideneacetone)dipalladium(0) (0.238 g, 0.26 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.231 g, 0.4 mmol) and potassium carbonate (5.72 g, 41.4 mmol) were stirred together. Added to this was a solution of 2-(4-methoxybenzyl)-3,3-dimethyl-1,2,5-thiadiazolidine 11-dioxide (8.00 g, 29.6 mmol) in dioxane (50 mL) and the resulting mixture stirred at 100 C. for 18 h. The cooled mixture was diluted with CH2Cl2 and the solids were removed by filtration. The solvent was evaporated leaving a yellow oil that was purified by flash chromatography (Biotage flash chromatography system, 5%-100% ethyl acetate/hexane) to give a cream colored solid that was triturated with ethyl acetate/hexane (1:4) to give the title compound as a white powder (4.6048 g, 42% yield). 1H NMR (500 MHz, CDCl3) delta: 7.71-7.65 (2H, m), 7.37 (2H, d, J=8.5 Hz), 7.12-7.08 (1H, m), 6.88 (2H, d, J=8.5 Hz), 4.28 (2H, s), 3.80 (3H, s), 3.78 (2H, s), 1.42 (6H, s).

According to the analysis of related databases, 36282-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/253677; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Diethyl 2-(2-cyanoethyl)malonate

(a) Diethyl 2-(2-cyanoethyl)-2-(5-nitropyrid-2-yl)malonate Sodium hydride (53% dispersion in oil) (30.71g, 0.66mole) was washed by decantation with xylene (2 * 150ml), ether (150ml), tetrahydrofuran (THF) (150ml) and finally suspended in THF (245ml). Diethyl 2-(2-cyanoethyl) malonate (156g. 0.73mole) in THF (80ml) was added dropwise over 1hr keeping the internal temperature at 18C to 22C (with ice bath cooling). The resulting suspension cleared over 15 minutes when 2-chloro-5-nitropyridine (88.3g, 0.55mole) was added to give a deep magenta solution. The resulting solution was refluxed for 1hr and the solvent was removed on the rotary evaporator. The resulting oil was partitioned between water (500ml) and chloroform (800ml), the pH was adjusted to ~7 (concentrated hydrochloric acid), and the chloroform was run off. The aqueous layer was extracted with a further (2 * 250ml) chloroform, the extracts were combined, dried over magnesium sulphate and the solvent was removed to give an amber oil (~245g). Ether (150ml) was added and the solution was allowed to crystallise to give the title compound (121.98g, 65%), m.p. 59.5-61C. (Found C, 53.7: H, 5.05; N, 12.35%. C15H17N3O6 requires C, 53.75; H, 5.1: N, 12.55%) NM, (CDCl3, 60 MHz); delta 1,37 (6H, t); 2.65 (4H, m); 4.26 (4H, q); 7.84 (1H, dd); 8,49 (1H, dd); 9.32 (1H, dd).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 17216-62-5.

Reference:
Patent; SMITH KLINE & FRENCH LABORATORIES, LIMITED; EP287270; (1988); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts