Tag: M.W=200-300

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, Product Details of 36282-26-5

Example 16 2-bromo-4-(2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)benzonitrile (Intermediate 16) Pyrrole (2,6,6-trimethyltetrahydroindol-4-one) (1.5 g, 8.5 mmol) and 2-bromo-4-fluorobenzonitrile (1.69 g, 8.5 mmol) are dissolved in anhydrous DMF (50 mL). To this NaH (95%, 408 mg, 17.0 mmol) is added and stirred at 50 C. for 1 h. The reaction mixture is cooled to RT and H2O is added. Product crashed out of solution and is filtered and dried under vacuo (2.4 g, 79%).

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; Hall, Steven E.; (44 pag.)US2015/329493; (2015); 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. 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H3BrN2O2

[00305] A microwave vial was charged with 1-propyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridin-2(1H)-one (0.200 g, 0.6 mmol), 2-bromo-5-nitrobenzonitrile (0.180 g, 0.8 mmol), and dioxan (8 mL) and water (2 mL) and the flask was degassed and flushed with argon. PdCl2(dppf) (0.058 g, 0.1 mmol) was added and the reaction flask was again degassed and flushed with argon. The reaction mixture was then heated to 100C in a microwave for 45 minutes. The reaction was cooled to room temperature and quenched with sat. NaHC03 and extracted with ethyl acetate (3X50 mL). The combined organics were washed with water, brine and dried over MgS04. The solvents were evaporated to dryness and the residue purified by flash chromatography (silica gel, 0-60% ethyl acetates in hexanes) to afford the product as yellow solid (170 mg, 80%). LC/MS: [M+l]+, 350.2; 1H NMR (300 MHz, CDC13): delta 8.60 (d, J=2.4 Hz, IH), 8.47 (t, J=2.4 Hz, IH), 8.44 (d, J=2.4 Hz, IH), 8.15 (s, IH), 7.84-7.82 (m, 2H), 7.70-7.65 (m, IH), 6.71 (d, J=9.9 Hz, IH), 3.98 (t, J=7.5 Hz, 2H), 1.89-1.81 (m, 2H), 1.02 (t, J=6.9 Hz, 3H).

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; FGH BIOTECH, INC.; HUFF, Joel; UESUGI, Motonari; KINCAID, John; (213 pag.)WO2017/190086; (2017); 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. 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, A new synthetic method of this compound is introduced below., Recommanded Product: 52133-67-2

Acetamidine hydrochloride (413 mg, 4.4 mmol) was added to a solution of sodium ethoxide (594 mg, 2.0 equiv.) in ethanol (8 mL). After stirring for half an hour at room temperature, the resultant sodium chloride was removed by filtration. The filtrate was added to ethyl 2-cyano- 4,4-diethoxybutanoate (1.0 g, 4.4 mmol) and the mixture was refluxed for 5 hours. Most of the solvent was removed and the remaining slurry was dissolved in ice water, and extracted with ethyl acetate. The extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (100percent methanol). The desired product was obtained as a red solid (421 mg, 40percent). MS: (M + H)/z = 242.

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; CHEMOCENTRYX, INC.; WO2009/9740; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 49674-15-9, name is 3-Bromo-5-nitrobenzonitrile, 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 49674-15-9, HPLC of Formula: C7H3BrN2O2

General procedure: To a solution of 6 (500 mg, 2.64 mmol) in 10 mL of DMF was successively added Et3N (1.47 mL, 10.56 mmol), 9a (600 mg, 2.64 mmol), CuI (50 mg, 0.26 mmol), and trans-dichlorobis(triphenylphosphine)palladium (184 mg, 0.26 mmol). The resulting solution was warmed to 60 oC, and TBAF 1M in THF (2.9 ml, 2.90mmol) was added dropwise. After 2h at this temperature the mixture was hydrolyzed with 50 mL of H2O and, extracted with AcOEt (4 X 30 mL). The organic layer was washed with saturated NaCl (3 X 30 mL), dry over anhydrous Na2SO4, and concentrated on a rotary evaporator. Purification of the residue by column chromatography (hexane/AcOEt 8/2) yielded 473 mg (68 %) of 2a as an off white solid.1H NMR (CDCl3), d = 2.50 (s, 3H, CH3); 7.13 (d, 1H, J=7.6 Hz, CHAr); 7.32 (d, 1H, J=7.6 Hz, CHAr); 7.56 (t, 1H, J=7.6 Hz, CHAr); 8.04 (t, 1H, J=1.6 Hz, CHAr); 8.35 (t, 1H, J=1.6 Hz, CHAr); 8.52 (t, 1H, J=1.6 Hz, CHAr). 13C NMR (CDCl3), d = 24.5 (1C, CH3); 83.4 (1C, C?C); 93.6 (1C, C?C); 114.4 (1C, Cq); 115.9 (1C, Cq); 124.4 (1C, CHAr); 124.9 (1C, CHAr); 126.1 (1C, Cq); 126.4 (1C, CHAr); 130.3 (1C, CHAr); 136.7 (1C, CHAr); 140.1 (1C, CHAr); 140.7 (1C, Cq); 148.1 (1C, Cq); 159.5 (1C, Cq). Anal (C15H9N3O2, HCl) C, H, N.

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

Reference:
Article; Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3243 – 3247;,
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Application of 1813-33-8, 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. 1813-33-8 name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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.

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).

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

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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Related Products of 2286-54-6, A common heterocyclic compound, 2286-54-6, name is 3,3-Diphenylpropanenitrile, molecular formula is C15H13N, 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.

General procedure: Gaseous hydrogen chloride was bubbled through a solution of 35.8 g (0.185 mol) of 3,4,5-trimetoxy-benzonitrile and 15 mL of anhydrous ethanol in 150 mL of diethyl ether cooledto 0-5C until a gain in weight of 8 g. The mixture was kept for 48 h at 3-5C, and the precipitate was filtered off and washed with diethyl ether (3 × 20 mL). Yield of 1a hydrochloride 45.7 g (89%). The product was mixed with 100 mL of water and 150 mL of diethyl ether, the mixture was cooled to 4-8C, and 15 g of sodium hydrogen carbonate was added with stirring. The mixture was stirred for 10 min, the organic phase was separated and dried over anhydrous sodium sulfate, and the solvent was distilled off. Yield 38g (85%).

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; Khromova, N. Yu.; Fedorov; Malekin; Kutkin; Russian Journal of Organic Chemistry; vol. 52; 10; (2016); p. 1490 – 1495; Zh. Org. Khim.; vol. 52; 10; (2016); p. 1497 – 1502,6;,
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Related Products of 846023-24-3, These common heterocyclic compound, 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, 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.

Reference Example 2; 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl )-3-r(3-iodo-4-methoxyphenv?amino1- prop-2-enamide; To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (5.00 g, 19.30 mol) in 400 ml_ of /so-propanol, under N2, is added 3-iodo-p-anisidine (5.80 g, 23.16 mmol). This mixture is heated to reflux to give a clear yellow solution. To this solution, triethylorthoformate (8.60 ml_, 52.11 mmol) is added dropwise and the reaction mixture is heated at reflux overnight. An additional 10 ml_ of triethylorthoformate is added and the mixture is heated at reflux overnight. The mixture is allowed to cool to room temperature and the white solid is collected by filtration, washing with /so-propanol, and dried overnight at -4O0C under reduced pressure. Purification by suspension in hot ethyl acetate followed by addition of cold hexanes gives 8.50 g (85%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(3-iodo- 4-methoxyphenyl)amino]prop-2-enamide as a yellow solid, mp 289-290 0C; MS (ES) m/z 516.7 (M-H)-. Analysis for C18H14CI2IN3O3:Calcd: C, 41.73; H, 2.72; N, 8.11. Found: C, 40.88; H, 2.64; N, 7.90.

Statistics shows that 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide is playing an increasingly important role. we look forward to future research findings about 846023-24-3.

Reference:
Patent; WYETH; WO2006/47262; (2006); A1;,
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These common heterocyclic compound, 39786-34-0, name is Ethyl 2-(2-cyanophenoxy)acetate, 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. Safety of Ethyl 2-(2-cyanophenoxy)acetate

To a 1000 mL flask 50.0 g (244 mmol) of the intermediate product (L-1) was added, stirred and 6.43 g (268 mmol) of sodium hydride in 500 ml of DMF (dimethylformamide) are added slowly at 0C. The reaction was allowed to proceed to room temperature for 10 hours. After confirming the completion of the reaction by TLC, 500 mL of dichloromethane and 2000 mL of distilled water were injected to separate the organic layer, and concentrated under reduced pressure to obtain 37.0 g (yield 64%) of intermediate L-2.

The synthetic route of Ethyl 2-(2-cyanophenoxy)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEIL INDUSTRIES INC.; JEONG, SOO-YOUNG; YU, EUN-SUN; KANG, DONG-MIN; SHIN, JI-HUN; RYU, DONG-KYU; LEE, SANG-SHIN; LEE, HAN-IL; JANG, YU-NA; HAN, SU-JIN; HONG, JIN-SEOK; (35 pag.)KR2015/17817; (2015); A;,
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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 72035-46-2 as follows. Quality Control of 2,3-Bis(4-methoxyphenyl)propanenitrile

In the first step, formation of the substituted stilbene occurred through basic addition of 2-(4-methoxyphenyl)acetonitrile to 4-methoxybenzaldehyde in high yield. Reduction of the stilbene using NaBH4 to afford 2,3-bis(4-methoxyphenyl)propanenitrile was followed bytreatment with BBr3 to cleave the methyl ethers, giving DPN in high yield.DPN was then acetylated using acetic anhydride to provide Compound 1. Either the corresponding anhydride or acyl chloride was used to provide Compounds 2-6.For an exemplary synthesis of the R-enantiomer of DPN, see Carroll, VM. et al., J. Med. Chem. 2012 55:528-537.

According to the analysis of related databases, 72035-46-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; JUNG, Michael, E.; VOSKUHL, Rhonda, R.; (58 pag.)WO2018/49094; (2018); A1;,
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Related Products of 1835-65-0, 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 1835-65-0 as follows.

EXAMPLE 1 After loading 5.0 g (25.0 mmol) of tetrafluorobenzene-o-dicarbonitrile (melting point: 86° C., Fluorochem Co.) and 4.15 g (25.0 mmol) of potassium iodide into a 100 ml 3-necked flask equipped with a reflux condenser tube, the interior of the flask was exchanged with nitrogen. To this was added 35 ml of dimethylformamide prior to reaction at 140° C. for 3 hours. Upon analysis of the reaction solution by gas chromatography (OV17 column, product of Shimazu Laboratories), 2,2′,5,5′,6,6′-hexafluorobiphenyl-3,3′,4,4′-tetracarbonitrile was found to be produced with a tetrafluorobenzene-o-dicarbonitrile conversion rate of 63percent and 83percent selectivity. After cooling the reaction mixture to room temperature, 150 ml of ethyl acetate was added and the solution was washed with a 3percent aqueous hydrochloric acid solution and then with a 10percent aqueous sodium thiosulfate solution. After distilling off the ethyl acetate, the residue was purified by column chromatography (silica gel/toluene:hexane=7:3) to obtain 2.10 g of 2,2′,5,5′,6,6′-hexafluorobiphenyl-3,3′,4,4′-tetracarbonitrile. The yield was 46percent. The product analysis values were as follows. MS measurement, M+: 362

According to the analysis of related databases, 1835-65-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ube Industries, Ltd.; US5856557; (1999); A;,
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