Tag: M.W=200-300

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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C14H10N2O2

To a stirred solution of intermediate 11 (0.5g, 1.996 mmol) and diphenyl cyanocarbonimidate (0.475 g, 1.996 mmol) in acetonitrile (30 mL) was added triethylamine (0.0.833 mL, 5.988 mmol) at RT and stirred for l6h at RT. After completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was purified by combiflash column on silica gel (hexanes/ethyl acetate=75/25) to give the title compound (0.5 g, 70%). LCMS: m/z 358.2 [M]+

According to the analysis of related databases, 79463-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak V.; RAMACHANDRA, Muralidhara; SATYAM, Leena Khare; (139 pag.)WO2019/142126; (2019); A1;,
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Application of 867366-91-4, 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. 867366-91-4, name is 3-Bromo-5-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

3-bromo-5- methoxybenzonitrile (8.3 g, 39.1 mmol),dicyclohexyl(2′,6′-dimethoxy-[l, -biphenyl]-2- yl)phosphine (S-Phos) (1.286 g, 3.13 mmol), phenylboronic acid (5.84 g, 47.0 mmol), Pd2(dba)3 and 200 mL toluene were charged in a flask and refluxed overnight. The reaction was cooled down and 200 mL of ethyl acetate was added. The crude mixture was run though a silica gel plug, and the product was confirmed by GC. After distillation under vacuum, 7.5 g of a white product was obtained.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-methoxybenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; XIA, Chuanjin; YEAGER, Walter; LI, David Zenan; FIORDELISIO, James; MA, Bin; ELSHENAWY, Zeinab; LAYEK, Suman; BARRON, Edward; KOTTAS, Gregg; BROOKS, Jason; WO2012/116231; (2012); A2;,
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Application of 70591-86-5,Some common heterocyclic compound, 70591-86-5, name is 3-Bromobenzoylacetonitrile, 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.

3- (3-bromophenyl)-JH-pyrazol-5-amine: A mixture of 3 -(3 -bromophenyl)-3 – oxopropanenitrile (35 g, 156 mmol) and hydrazine hydrate (11.34 mL, 234 mmol) inethanol (600 mL) was refluxed for 16 h. Mixture was then cooled and concentratedin vacuuo. Crude product was diluted with dichloromethane and stirred for 5 mm.Solids were filtered and dried to afford 3-(3-bromophenyl)-1H-pyrazol-5-amine (30g, 126 mmol, 81 % yield) as off-white solid. ?H NMR (400 MHz, DMSO-d6) oe 12.02(br. s., 0.4H), 11.66 (br. s., 0.6H), 7.86 (t, J1 .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.

The synthetic route of 70591-86-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NAIDU, B. Narasimhulu; PATEL, Manoj; D’ANDREA, Stanley; ZHENG, Zhizhen Barbara; CONNOLLY, Timothy P.; LANGLEY, David R.; PEESE, Kevin; WANG, Zhongyu; WALKER, Michael A.; KADOW, John F.; WO2015/126376; (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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

2-Phenyl-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridine hydrochloride (purchased from Anichem) (150mg, 0.63 mmol), tris(dibenzylideneacetone)dipalladium(0) (40 mg, 0.04 mmol), BINAP (97 mg, 0.16 mmol) and 3-bromo-5-fluorobenzonitrile (126 mg, 0.63 mmol) were combined in toluene (3 mL). The mixture was first flushed with nitrogen before and after the addition of sodium tert-butoxide (73 mg, 0.76 mmol). The solution was heated at 1200C under nitrogen overnight. The solvent was concentrated and removed under vacuum. The residue was then purified by silica gel column (EtOAc (10% MeOEta)/hexanes), followed by recrystallization in methanol to give a white solid (10 mg, 5%). 1H NMR (400 MHz, CDCl3): delta 8.01 (m, 2H), 7.46 (m, 3H), 6.97 (s, IH), 6.81-6.85 (m, IH), 6.78 (m, IH), 4.32 (m, 2H), 3.77 (t, 2H), 2.95-2.98 (m, 2H); LC/MS: m/e = 320 (M+H)+.

According to the analysis of related databases, 179898-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
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144649-99-0, name is 5-Bromo-2-methoxybenzonitrile, 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: 144649-99-0

Example 35 1,1-Dimethylethyl {[5-bromo-2-(methyloxy)phenyl]methyl}carbamate NaBH4 (2.9 g, 75.5 mmol) was cautiously added in several portions to a solution of NiCl2 (2.6 g, 19.8 mmol), Boc2O (8.2 g, 37.7 mmol) and 5-bromo-2-(methyloxy)benzonitrile (4.0 g, 18.9 mmol) in dry EtOH (70 mL) at 0 C. Once the reaction had subsided, the mixture was left to stir at room temperature for 3 h. Ethanol was removed under reduced pressure and the residue was dissolved in EtOAc and saturated solution of NaHCO3, then filtered and the aqueous layer was repeatedly washed with EtOAc. The combined organic phases were dried Na2SO4. The crude product was purified by flash column chromatography to give the captioned the product (1.5 g yield: 25%). 1H NMR (400 MHz, CDCl3) delta 7.36-7.33 (m, 2H), 6.74 (d, J=8.8 Hz, 1H), 4.97 (br, 1H), 4.27 (d, J=4.8 Hz, 1H), 3.82 (s, 3H), 1.45 (s, 9H); 13C NMR (400 MHz, CDCl3) delta 156.5, 155.8, 131.7, 131.1, 129.3, 111.8, 79.5, 55.5, 39.9, 26.4. HPLC: retention time.

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

Reference:
Patent; Glaxo Group Limited; US2009/203657; (2009); A1;,
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Synthetic Route of 1953-99-7,Some common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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 100 mL flask was added the solid (4- (biphenyl-2-ylamino) -3,5,6-trichlorophthalonitrile (1.0 g), 3,4,5,6-tetrachlorophthalonitrile (0.22 g), 1,8-Diazabicycloundec- -ene (1.0 g), and 1-pentanol (10 mL), and dissolve by heating. Then, zinc acetate (0.15 g) is added and refluxed with heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. At this time, the obtained solid is filtered and vacuum dried to obtain a compound represented by the following formula (C).

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co.,Co.,Ltd; Kwon, Jae Young; Jung, Ju Ho; Lee, Yeon Soo; Lee, Jung Sun; Lee, Chang Ryul; (35 pag.)KR2016/22080; (2016); A;,
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Application of 1211596-75-6, The chemical industry reduces the impact on the environment during synthesis 1211596-75-6, name is Methyl 2-cyano-3-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

Reference Example 6 Synthesis of 2-cyano-3-(trifluoromethyl)benzoic acid In accordance with the manner of Reference Example 5, the title compound was obtained from 248 mg of methyl 2-cyano-3-(trifluoromethyl)benzoic acid.

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, Methyl 2-cyano-3-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP2017279; (2009); 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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-4-fluorobenzonitrile

3,6,6-Trimethyl-6,7-dihydro-1 H-indazol-4(5H)-one (0.535 g, 3 mmol) was dissolved in dry DMSO (15 mL). Sodium hydride (0.15 g, 3.75 mmol) was slowly added. After H2 evolution ceased, 2-bromo-4-fluorobenzonitrile (0.900 g, 4.50 mmol) was added. The resulting mixture was heated at 45 C overnight, cooled, poured into satd. NH4CI solution (50 ml), and extracted with EtOAc three times. The combined organic phases were washed with water/brine, dried over MgS04, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% – 50% EtOAc in hexanes) to afford the title compound as a white solid (0.65 g, 60.5%). 1 H NMR (400 MHz, CHLOROFORM-d) delta 8.01 (d, J = 2.15 Hz, 1 H), 7.82 (d, J = 8.61 Hz, 1 H), 7.63 (dd, J = 2.15, 8.42 Hz, 1 H), 2.90 (s, 2H), 2.59 (s, 3H), 2.47 (s, 2H), 1 .18 (s, 6H). LCMS: fR = 0.90 min, 100%. MS (ESI): m/z 358, 360 (M+H)+.

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; GLAXOSMITHKLINE LLC; TEMPERO PHARMACEUTICALS, INC.; GHOSH, Shomir; LOBERA, Mercedes; POHLHAUS, Denise, Teotico; TRUMP, Ryan, Paul; ZHANG, Cunyu; WO2013/66831; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-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 36282-26-5, Recommanded Product: 2-Bromo-4-fluorobenzonitrile

Example 21 1-amino-6-fluoro-isoquinoline-4-carbonitrile; Palladium acetate (II) (0.556 g, 2.5 mmol) is added to a degassed solution of 2-bromo-4-fluoro-benzonitrile (10 g, 50 mmol), 3-ethoxyacrylonitrile (10.3 mL, 100 mmol) and triethylamine (14 mL, 100 mmol) in toluene (75 mL). The reaction mixture is stirred in an oil bath at 100 C. for 1 day. The reaction mixture is cooled to RT, filtered through a pad of Celite, and the filter cake is rinsed with EtOAc. After evaporation of the solvent, the residue is purified using a Biotage column eluted with 0-50% EtOAc/hexanes (20 CV) to afford 8.77 g (94%) of 2-(1-cyano-2-ethoxy-vinyl)-4-fluoro-benzonitrile. LC/MS: RT=3.38 min, no ionization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Huang, Kenneth He; Veal, James; Barta, Thomas; Smith, Emilie D.; Ma, Wei; Ommen, Andy; US2008/70935; (2008); 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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3BrFN

To a solution of 2-bromo-4-fluorobenzonitrile (0.30 g, 1.5 mmol) and cyclopropanol (0.14 g, 2.4 mmol) in DMF (4 mL) wasadded Cs2CO3 (0.88 g, 2.7 mmol) in a 25 mL single-necked round-bottom flask. After that, themixture was stirred at 25 C under nitrogen. After stirring for 4 h, the resulting mixture was dilutedwith H2O (30 mL) and extracted with MTBE (10 mL×3). Then the combined organic phase waswashed with saturated aqueous NaCl (10 mL×3) and dried over Na2SO4 for 0.5 h. After that, theorganic phase was filtered under reduced pressure and the filtrate was concentrated underreduced pressure to give product as a yellow sticky substance. Then a mixture of 30 mL MTBE and100 mL n-hexane was added to dissolve the yellow sticky substance. Subsequently, the solutionwas cooled for 30 minutes with the mixture of water and ethanol. Lastly, the solution was filteredunder reduced pressure and the filtrate was dried naturally to obtain desired product in 80.3%yield (0.29g).

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; Jin, Hao; Gao, Zhuo; Zhou, Shaodong; Qian, Chao; Synlett; vol. 30; 8; (2019); p. 982 – 986;,
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