Author: Jessica.F

Application of 19295-57-9, 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 19295-57-9 as follows.

Preparation No.6: 3-Methoxy-2,2-dimethylpropylamine HCl; To a mixture of sodium tetrahydroborate (7.4 g, 200 mmol) in EtOH (100 mL) at about 0 0C was added cyanodimethylacetic acid ethyl ester (TCI, 10.0 g, 70.8 mmol) in EtOH (100 mL) over about EPO 45 min. The mixture was allowed to warm to ambient temperature over about 30 min. After about 60 h, the solvents were removed in vacuo. The resulting material was treated with saturated aqueous NH4Cl (150 mL) and extracted using DCM (3 x 30 mL). The combined organic layers were dried over Na2SO4 and concentrated to yield the crude 3-hydroxy-2,2-dimethylpropionitrile (8.61 g). A mixture of crude 3-hydroxy-2,2-dimethyl-propionitrile (1.0 g, 10 mmol) in DCM (40 mL) was treated with tetrafluoroboric acid (1.4 g, 10 mmol) followed by 2 M trimethylsilyldiazomethane in heptane (5.0 mL, 10 mmol) at about 0 0C over about 10 min. The mixture was treated with additional 2 M trimethylsilyldiazomethane in heptane (2 mL, 4.0 mmol) after about 20 min, followed by additions of 2 M trimethylsilyldiazomethane in heptane (1.3 mL, 2.6 mmol) and 2 M trimethylsilyldiazomethane in heptane (1.3 mL, 2.6 mmol) after about 20 min intervals sequentially. The mixture was allowed to stir at about 0 0C for about 50 min before it was poured slowly over water. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were washed with water, dried over Na2SO4, and concentrated to yield the crude 3- methoxy-2,2-dimethylpropionitrile as a yellow oil (1.2 g). Into a Parr shaker vessel was added crude 3-methoxy-2,2-dimethylpropionitrile (1.0 g, 8.8 mmol), 33% aqueous ammonium hydroxide (75 mL), MeOH (10 mL), and 8.0 M Raney nickel in water (1 mL, 8.0 mmol). The materials were charged with hydrogen and shaken at ambient temperature. After about 16 h, the mixture was filtered over Celite and treated with 5 M sodium hydroxide in water (2 mL), di-tert- butyldicarbonate (2.3 g, 11 mmol), and EtOAc (75 mL). After about 5 h, the layers were separated and the aqueous layer was washed with DCM. The combined organic layers were washed with water then dried over Na2SO4 and concentrated in vacuo. The residue was purified via FCC using EtO Ac/heptane (1:4). The fractions containing product, as visualized on TLC with ninhydrin stain, were concentrated in vacuo to yield (3-methoxy-2,2-dimethylpropyl)-carbamic acid tert-butyl ester, which was treated with 1.25 M HCl in methanol (1 mL) at ambient temperature. After about 2 h, the mixture was concentrated in vacuo to give methoxy-2,2-dimethylpropylamine HCl: (0.090 g): 1H NMR (DMSO-d6, 400 MHz) 6 3.85-3.75 (2H), 3.26 (3H), 3.13 (2H), 2.65-2.70 (2H), 0.91 (6H); TLC (acetone/MeOH 95:5) Rf = 0.2.

According to the analysis of related databases, 19295-57-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/28051; (2007); A2;,
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Reference of 500912-18-5, 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 500912-18-5 as follows.

A mixture of 6-chloro-4-(ethyl amino) nicotinaldehyde (Scheme 1 compound 6) (1.7 g, 9.32 mmol), Scheme 56 compound 4 (2.0 g, 12.11 mmol) and K2C03 (3.8 g, 27.96 mmol) in dry DMF (10 mL) was heated to 100 C under nitrogen atmosphere for 16 h. After TLC showed the starting material was completely consumed, the reaction mixture was cooled to RT, diluted with EtOAc (2 x 50 mL), washed with water (2 x 20 mL) and brine (10 mL) then dried over Na2S04 and concentrated to give a residue which was purified by flash chromatography on silica gel (eluting with petroleum ether/EtOAc 100/0 gradually increasing to 60/40) to give 7-chloro-l-ethyl-3-(2-fluoro-6-methoxyphenyl)-l,6-naphthyridin-2(lH)- imine (800 mg, 26%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 8.41 (s, 1H), 7.51 (q, J= 8.0 Hz, 1H), 7.41 (d, J= 10.6 Hz, 2H), 7.07-6.92 (m, 2H), 4.26 (m, 2H), 3.77 (d, J = 2.4 Hz, 3H), 1.22-1.16 (m, 3H). MS [ESI, MH+] = 332.09.

According to the analysis of related databases, 500912-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MANNKIND CORPORATION; TOLERO PHARMACEUTICALS, INC.; ZENG, Qingping; FARIS, Mary; MOLLARD, Alexis; WARNER, Steven L.; FLYNN, Gary A.; WO2014/52365; (2014); A1;,
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Application of 133541-45-4, A common heterocyclic compound, 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, molecular formula is C7H2BrF2N, 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 stirred suspension of 4-bromo-2,5-difluorobenzonitrile (5.0 g, 22.9 mmol) and potassium carbonate (9.5 g, 68.8 mmol) in N,N-dimethylformamide (45.9 ml) was added (S)-1 ,1 ,1 – trifluoropropanol [CAS 3539-97-7] dropwise (2.88 g, 25.2 mmol). The resulting mixture was heated at 55 “C for for 15 hours and cooled to room temperature. Water (100 ml) was added to the mixture and extracted with diethyl ether (3chi50 ml). The combined organic extracts were sequentially washed with water (2chi100 ml), brine (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to give an off white solid (6.93 g). The residue was purified by flash column chroamtography to give the ether as a white crystalline solid (5.90 g, 97 % purity, 80 %).LC-MS (method A): R, = 1 .29 min; MS (ESIpos): m/z = 312.0 [M+H]+1H-NMR (400 MHz, CHLOROFORM-d) delta [ppm]: 1 .51 1 (4.41 ), 1.531 (15.64), 1 .533 (16.00), 1 .548 (15.84), 1.550 (15.83), 4.566 (1.08), 4.581 (2.68), 4.597 (3.18), 4.612 (2.62), 4.626 (1 .01 ), 7.194 (5.27), 7.207 (7.60), 7.220 (7.57).

The synthetic route of 133541-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE GENERAL HOSPITAL CORPORATION; GRADL, Stefan, Nikolaus; NGUYEN, Duy; EIS, Knut; GUENTHER, Judith; STELLFELD, Timo; JANZER, Andreas; CHRISTIAN, Sven; MUELLER, Thomas; EL SHEIKH, Sherif; ZHOU, Han, Jie; ZHAO, Changjia; SYKES, David B; FERRARA, Steven, James; LIU, Kery; HERBERT, Simon, Anthony; MERZ, Claudia; NIEHUES, Michael; NISING, Carl, Friedrich; SCHAeFER, Martina; ZIMMERMANN, Katja; KNAEBLEIN, Joerg; THEDE, Kai; FAUPEL, Thomas; (539 pag.)WO2018/77944; (2018); A2;,
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Application of 69975-66-2, 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. 69975-66-2, name is 3-Oxo-indan-5-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a series of 1.5 mL glass tubes was added amine 5 or 6 in NMP (0.95 M, 0.095 mmol), followed by solutions of different indanones (0.5 M, 0.1 mmol) in NMP, and these mixtures were subsequently treated with acetic acid (0.1 mmol), followed by 5-ethyl-2-methylpyridineborane (PEMB) (0.2 mmol). The reaction mixture was heated at 65 C on a reaction block for 24 h. The reaction mixtures were purified directly using an automated mass-guided reverse phase HPLC, and product containing fractions were concentrated to give final products of >90% purity as judged by LC-MS (average of 220 and 254 nm traces).

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

Reference:
Article; Vilums, Maris; Zweemer, Annelien J. M.; Barmare, Farhana; Van Der Gracht, Anouk M. F.; Bleeker, Dave C. T.; Yu, Zhiyi; De Vries, Henk; Gross, Raymond; Clemens, Jeremy; Krenitsky, Paul; Brussee, Johannes; Stamos, Dean; Saunders, John; Heitman, Laura H.; Ijzerman, Adriaan P.; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 121 – 134;,
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Reference of 6283-71-2, 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. 6283-71-2, name is Dimethyl 2-cyanosuccinate, This compound has unique chemical properties. The synthetic route is as follows.

Cyanodiester 12 (1.16 g; 6.78 mmol) was dissolved in ethanol/water 1:1 (12 mL), cooled to 0-5 C and Et3N (1.2 mL) was added dropwise. After 15 min tert-butyl acrylate (1.05 mL; 0.92 g; 7.14 mmol) was added dropwise. The mixture was stirred at 0-5 C for 1.5 h, allowed to warm to room temperature and stirred for further 2 h. It was then concentrated, diluted with water, acidified with 2 N HCl to pH 4 and extracted 3* with AcOEt. The combined organic extracts were dried with MgSO4, concentrated in vacuo and chromatographed on silica gel in hexane/AcOEt (4:1) to give 20 (0.61 g; 29%; Rf 0.27) and 21 (0.77 g; 38%; Rf 0.23) as colourless oils.

The chemical industry reduces the impact on the environment during synthesis Dimethyl 2-cyanosuccinate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Weinberg, Kamil; Stoit, Axel; Kruse, Chris G.; Haddow, Mairi F.; Gallagher, Timothy; Tetrahedron; vol. 69; 23; (2013); p. 4694 – 4707;,
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These common heterocyclic compound, 38469-84-0, name is 5-Methoxy-2-nitrobenzonitrile, 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. name: 5-Methoxy-2-nitrobenzonitrile

General procedure: Condition B: An oven-dried pressure tube (10 mL) was charged with sodium sulfide nonahydrate (144 mg, 0.6 mmol), acetic acid (36 mg, 0.6 mmol), nitrobenzene (24.6 mg, 0.2 mmol), DMF (0.8 mL). The reaction vessel was closed under air and the resulting solution was stirred at room temperature for 20 h. Then the reaction mixture was filtered through a pad of silica gel and washed with 5 mL ethyl acetate for three times. The filtrate was removed under vacuum and the residue was purified by flash column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to give the desired product.

The synthetic route of 5-Methoxy-2-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shuai, Qi; Li, Jun; Zhao, Feng; Su, Weike; Deng, Guojun; Chemical Papers; vol. 73; 4; (2019); p. 965 – 975;,
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Synthetic Route of 38791-62-7, 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. 38791-62-7, name is 4-Phenoxyphthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1,2-Diisocyano-4-phenoxy benzene (8) (0.300 g, 1.36 ×10-3 mol) and phenol (0.356 g, 0.0375 mol) in THF was refluxed. The resultant product (9), 1,2-diisocyano-3,4-diphenoxy benzene,(0.300 g, 1.36 × 10-3 mol) was refluxed in 1-pentanol (14 mL)and 1 mol 1,8-diazabicyclo[5.4.0]-undec-7-ene (0.21 g, 1.36× 10-3 mol) for 16 h. Methanol (20 mL) was there after added and the precipitate (2a) filtered off, Soxhlet extracted with methanol and acetone and dried at 60 C. Yield = 0.294 g and yield (%) 43, Rf = 0.23 (ethyl acetate:hexane, 3:8). (KBr, numax,cm-1): 3620 (N-H), 2848 (C-H) aromatic, 1685 (C=C), 1163(C-H), 743 (C-H). UV-visible lambdamax (nm): 337, 606, 640, 661,702. 1H NMR (300 MHz, CDCl3) delta 2.01 (s, 2H, NH), 3.66 (m,4H, CH), 6.99 (m, 4H, ArH), 7.23 (m, 4H, ArH), 7.50 (m, 4H,ArH) 8.04 (m, 4H, ArH), 8.99 (m, 4H, ArH), 9.23 (m, 4H,ArH), 13C NMR (300 MHz, CDCl3) delta 71.01, 76.57, 76.99,77.41, 117.45, 119.69, 119.92, 126.95, 127.48, 127.63, 128.53,128.85, 128.94, 134.43, 135.20. Anal. calcd. C, 76.21; H, 4.19;N, 9.03. Found: C, 76.21; H, 4.18; N, 9.11.

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, 4-Phenoxyphthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Isabirye, David A.; Seheri, Naledi H.; Aiyelabola, Temitayo O.; Asian Journal of Chemistry; vol. 29; 3; (2017); p. 489 – 495;,
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Application of 447-60-9, 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 447-60-9 as follows.

Step B 7-Chloro-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one; [Show Image] A 1.8 M lithium diisopropylamide THF solution (45.3 ml, 81.6 mmol) was diluted with THF (68 ml). Thereafter, a solution obtained by dissolving the 5-chloro-2,N-dimethylbenzamide (5.0 g, 27.2 mmol) prepared in step A in THF (28 ml) was added dropwise to the diluted solution at -78C. Thereafter, a solution obtained by dissolving 2-trifluoromethylbenzonitrile (4.65 g, 27.2 mmol) in THF (28 ml) was further added thereto, and the obtained mixture was then stirred at -78C for 2.5 hours. The temperature of the reaction solution was increased to a room temperature, and a saturated ammonium chloride aqueous solution was added thereto, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate. Thereafter, a solid generated as a result of vacuum concentration was filtrated, so as to obtain 7-chloro-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (6.87 g; yield: 78%) in the form of a colorless solid. 1H-NMR (270MHz, CDCl3) delta (ppm): 6.49 (1H, s), 7.33-7.72 (5H, m), 7.81-7.84 (1H, d, J=7.26Hz), 8.32-8.33 (1H, d, J=1.65Hz), 9.18 (1H, brs) ESI (LC-MS positive mode) m/z 324 (M+H).

According to the analysis of related databases, 447-60-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1854792; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, 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 138642-47-4, Computed Properties of C8H6BrNO

B. Synthesis of 5-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile A mixture of 2-bromo-5-methoxybenzonitrile (82.6 g, 0.39 mol, 1 equiv), bis(pinacolato)diboron (109.1 g, 0.43 mol, 1.1 equiv) and potassium acetate (115.3 g, 1.17 mol, 3 equiv) in a mixture of 1,4-dioxane (400 mL) and DMSO (40 mL) was sparged with nitrogen for 1 hour. Pd(dppf)Cl2 (7.13 g, 5 mol %) was added and reaction mixture was gently heated at 60 C. for 2 hours then refluxed for 16 hours. The mixture was filtered through celite and the solids isolated from the filtrates were washed with isopropanol and heptanes to give the desired product as an off-white solid (57.41 g, 57% yield). Additional product (?10 g) was isolated from the filtrates.

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-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; BROOKS, Jason; SZIGETHY, Geza; MORELLO, Glenn; DENG, Jun; DJUROVICH, Peter I.; CHEN, Hsiao-Fan; (206 pag.)US2016/72082; (2016); A1;,
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Electric Literature of 129931-47-1, 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. 129931-47-1, name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(i) 1-(2-Chloro-6-cyano-4-trifluoromethylphenyl)-5-bromo-4-trifluoromethyl-2-pyridone (Compound No 16 in Table II) was prepared by the reaction of 3-chloro-4-fluoro-5-cyanotrifluoromethylbenzene and 5-bromo-4-trifluoromethyl-2-pyridone. 1 H NMR delta(CDCl3) 8.10 (1H,d); 8.01 (1H,d); 7.45 (1H,s); 7.13 (1H,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, 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Imperial Chemical Industries PLC; US5109004; (1992); A;,
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