Tag: M.W=200-300

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. 17354-04-0, name is 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 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.

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; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
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Synthetic Route of 5866-98-8, 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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 11A 6-Chloro-2-ethylamino-3-nitro-benzonitrile A solution of ethylamine in THF (2 M, 13.8 mL, 27.6 mmol) was added slowly to a solution of 2,6-dichloro-3-nitrobenzonitrile (3.0 g, 13.8 mmol) in THF (30 mL) at -5 C. After 1.5 h, the solution was diluted with EtOAc (150 mL) and washed with 0.5 N HCl and brine. Organics were dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography (8:1:1 hexanes/CHCl3/EtOAc) gave 2.57 g (82%) of the title compound as an orange solid. 1H NMR (400 MHz, CDCl3): delta 8.51 (br s, 1H), 8.30 (d, 1H, J=8.8 Hz), 6.78 (d, 1H, J=8.4 Hz), 3.89-3.97 (m, 2H), 1.41 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc’d for C9H8N3O2Cl, 226, 228; found 226, 228.

The synthetic route of 2,6-Dichloro-3-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Feng, Jun; Gwaltney, Stephen L.; Wallace, Michael B.; Zhang, Zhiyuan; US2005/272765; (2005); A1;,
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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 17354-04-0 as follows. name: 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile

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.

According to the analysis of related databases, 17354-04-0, the application of this compound in the production field has become more and more popular.

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

Some common heterocyclic compound, 916792-13-7, name is 4-Bromo-2-fluoro-5-methylbenzonitrile, molecular formula is C8H5BrFN, 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. Formula: C8H5BrFN

To a solution of 4-bromo-2-fluoro-5-methylbenzonitrile (10.0 g, 46.7 mmol) in N,N-dimethylacetamide (30 mL) was added Pd(dppf)Cl2 (5.1 g, 7.0 mmol) and MeOH (10 mL), followed by TEA (14.3g, 140.1 mmol). The mixture was heated at 90 C overnight under carbon monoxide (5 MPa). The mixture was cooled to RT and the mixture was diluted with water, extracted with EA. The combined organic layers were concentrated to give the crude product, which was purified by silica gel chromatography eluting with EA/petroleum ether from 5% to 10% to give methyl 4-cyano-5-fluoro-2-methylbenzoate (7.33 g, 81%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 916792-13-7, its application will become more common.

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); A1;,
Nitrile – Wikipedia,
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5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, 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. name: 2,6-Dichloro-3-nitrobenzonitrile

Example 4 Synthesis of 2-(2,6-Dichlorophenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-]isoquinoline-9-one A solution of 2,6-dichloro-3-nitrobenzonitrile (98.7 g, 0.455 mol) in EtOAc (910 mL) was cooled to 5 C. 40% Aqueous methylamine (79.5 mL, 1.14 mol) was added with vigorous mechanical stirring, keeping the temperature at 10-15 C. After addition was complete, stirring was continued for 3 h at the same temperature. More methylamine (16 mL, 0.23 mol) was added, and the mixture stirred for a further 1.5 h at room temperature. Water (300 mL) was added, followed by hexane (450 mL). The mixture was stirred for 15 min, filtered, and the solid washed with water and MeOH, to give 6-chloro-2-methylamino-3-nitrobenzonitrile (80.3 g, 83%), mp 167-170 C.

The synthetic route of 5866-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US6506769; (2003); B2;,
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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. 144649-99-0, name is 5-Bromo-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 144649-99-0

Compound 64 (E)-Methyl 3-(3-(N-((3′-cyano-4′-methoxy-[l,l’-biphenyl]-4- yl)methyl)cyclohexanecarboxamido)phenyl)acrylate [00430] A mixture of Intermediate 16 (500 mg, 0.99 mmol), 5-bromo-2-methoxy-benzonitrile (316 mg, 1.49 mmol), Cs2C03 (647 mg, 1.99 mmol), Pd(PPh3)4 (230 mg, 199 mmol) in DMF (6 mL) was degassed with vacuum/nitrogen cycles (3 chi), stirred at 90 C for 12 h, and then filtered. Saturated EDTA-2Na (20 mL) was added, and the reaction mixture was stirred for 1 h and then extracted with ethyl acetate (3 x20 mL). The combined organic layers were washed with water (3 x 15 mL) and brine (2×20 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by reverse-phase HPLC to give (E)-m ethyl 3-(3-(N-((3′-cyano-4′-methoxy- [l, l’-biphenyl]-4-yl)methyl)cyclohexanecarboxamido)phenyl)acrylate (110 mg, 22%) as a white solid. 1H MR (DMSO-i): delta 8.01 (d, IH), 7.96 (dd, IH), 7.58-7.70 (m, 5H), 7.42 (t, IH), 7.31 (d, IH), 7.24 (d, 2H), 7.17 (d, IH), 6.64 (d, IH), 4.89 (s., 2H), 3.95 (s, 3H), 3.71 (s, 3H), 2.19 (m, IH), 1.58-1.72 (m, 4H), 1.36-1.54 (m, 3H), 1.05-1.18 (m, IH), 0.89 (d, 2H); MS: 509.3 [M+H]+.

The synthetic route of 144649-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (228 pag.)WO2017/49172; (2017); A1;,
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Related Products of 70591-86-5, 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. 70591-86-5 name is 3-Bromobenzoylacetonitrile, 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 mixture of 3-(3-bromophenyl)-3-oxopropanenitrile (35 g, 156 mmol) and hydrazine hydrate (11.34 mL, 234 mmol) in ethanol (600 mL) was refluxed for 16 h. Mixture was then cooled and concentrated in vacuuo. Crude product was diluted with dichloromethane and stirred for 5 min. Solids were filtered and dried to afford 3-(3-bromophenyl)-1H-pyrazol-5-amine (30 g, 126 mmol, 81 % yield) as off-white solid. 1H NMR (400 MHz, DMSO-d6) delta 12.02 (br. s., 0.4H), 11.66 (br. s., 0.6H), 7.86 (t, J=1.6 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.45 (d, J=6.8 Hz, 1H), 7.37 – 7.18 (m, 1H), 5.78 (br. s., 1H), 5.08 (br. s., 1.2H), 4.68 (br. s., 0.8H). LCMS (M+H) = 240.1.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NAIDU, B. Narasimhulu; WANG, Tao; PEESE, Kevin; YIN, Zhiwei; ZHANG, Zhongxing; KADOW, John F.; PATEL, Manoj; WO2015/126743; (2015); A1;,
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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. 85068-32-2, name is 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H5F6N

Lithium bis(trimethylsilyl)amide (4.9 ml, 1 .0 M in THF, 4.9 mmol) was added dropwise to a solution of [3,5-bis(trifluoromethyl)phenyl]acetonitrile (1 .00 g, 3.95 mmol) and 1 ,4- dibromobutane (700 mI, 5.9 mmol) in THF (25 ml) at OO and the mixture was stirred for 2 h at room temperature. Lithium bis(trimethylsilyl)amide (4.9 ml, 1.0 M in THF, 4.9 mmol) was added and the mixture was stirred over night at room temperature followed by 3 h at 600. For the work-up, the mixture was poured into brine, extracted with ethyl acetate (3x) and the combined organic phases were dried and concentrated. The residue was purified by flash chromatography (hexanes/ethyl acetate 95:5) to give the title compound 866 mg (68 % yield). 1 H-NMR (400 MHz, DMSO-afe): d [ppm] = 8.18 (s, 2H), 8.16 (s, 1 H), 2.60-2.52 (m, 2H), 2.23- 2.13 (m, 2H), 1 .98-1.86 (m, 4H).

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 85068-32-2.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; BUCHGRABER, Philipp; AIGUABELLA FONT, Nuria; WITTROCK, Sven; LANGE, Martin; BADER, Benjamin; PRECHTL, Stefan; LIENAU, Philip; KOPITZ, Charlotte, Christine; NOWAK-REPPEL, Katrin; POTZE, Lisette; (388 pag.)WO2020/48830; (2020); A1;,
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Electric Literature of 170230-29-2, A common heterocyclic compound, 170230-29-2, name is 4-Bromo-3-ethylbenzonitrile, molecular formula is C9H8BrN, 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.

Description 27; 2-ethyl-2′-fluoro-4-biphenylcarboxylic acid (D27); A mixture of 4-bromo-3-ethylbenzonitrile (D25) (651 mg, 3.10 mmol), 2- fluorophenylboronic acid (867 mg, 6.20 mmol), palladiumtetrakistriphenylphosphine (359 mg, 0.31 mmol) and potassium carbonate (1.29 g, 9.30 mmol) in dimethylformamide (10 ml.) was heated to 170 0C in the microwave for 30 minutes. The mixture was allowed to stand at room temperature over a weekend before it was poured into a mixture of ice and saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (3 x 20 ml.) and the combined organics washed with brine, dried (phase separator) and evaporated. The residue was purified by silica chromatography, eluting 0-5 % EtOAc in hexane to give a colourless oil (655 mg). This material was added to ethanol (26 ml.) and water (6 ml.) followed by potassium hydroxide (1.62 g, 28.9 mmol) and the mixture heated to 90 0C for 17 h. The solvent was evaporated and the residue partitioned between ethyl acetate and 2M HCI. The organic layer was washed with further HCI before it was dried (phase separator) and concentrated in vacuo to give the title compound as a white solid (648 mg, 2.66 mmol). MS (ES”): Ci5H13FO2 requires 244; found 243 (M-H+).

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; GLAXO GROUP LIMITED; WO2008/74820; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 5A 3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenecarbonitrile 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]+.

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, 3-Bromo-5-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AiCuris GmbH & Co. KG; US2012/22123; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts