Tag: M.W=200-300

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 138642-47-4 as follows. HPLC of Formula: C8H6BrNO

Step A: 1-(2-Bromo-5-methoxyphenyl)methanamine 2-Bromo-5-methoxybenzonitrile (10.0 g, 47.2 mmol) was dissolved in dry tetrahydrofuran (100 mL) in a flame-dried flask and cooled in an ice bath. A solution of borane in tetrahydrofuran (75 mL, 75 mmol, 1.0 M) was added dropwise over a period of 30 minutes. The reaction mixture was stirred overnight at rt, then quenched slowly with ice water and Na2CO3 (saturated aqueous solution). After removal of THF, the residue was extracted with large amounts of EtOAc three times. The combined organic layers were washed with water, dried, and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product as a white powder (3.65 g, 36%). LCMS for C8H10BrNO (M+H)+: m/z=216.9, 219.0.

According to the analysis of related databases, 138642-47-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; US2010/190804; (2010); A1;,
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Electric Literature of 17354-04-0, 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 17354-04-0 as follows.

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;,
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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. 872091-83-3, name is Methyl 4-chloro-3-(cyanomethyl)benzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-chloro-3-(cyanomethyl)benzoate

Preparation 7 Methyl 4-chloro-3-(2-methoxy-2-oxoethyl)benzoateIn a 6-litre glass reactor, equipped with a reflux condenser, thermometer, pressure equalizing dropping funnel, and a mechanical stirrer was placed methyl 4-chloro-3- (cyanomethyl)benzoate (461.6 g, 2.2 mol) in methanol (759 ml, 18.7 mol). The mixture was heated to 50 0C. Chloro-trimethyl-silane (1135 ml, 9 mol) was added to this solution over 80 minutes. The mixture was refluxed for 5 hours. There was a heavy evolution of hydrogen chloride gas during this period. The mixture was left at EPO ambient temperature overnight. The solvent was evaporated. After cooling the residue was diluted with dichloromethane (1930 ml) and water (1930 ml). The mixture was stirred for 0.5 hour and the layers were separated. The aqueous phase was extracted with dichloromethane (1000 ml), that was combined with the organic layer, dried over Na2SO4, filtered and concentrated to give oil, which solidified. The residue was used in the next step without purification. (515.8 g, white crystal) Yield: 97.1 %

The synthetic route of 872091-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; WO2006/79857; (2006); 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 67197-53-9 as follows. Formula: C8H5Br2N

EXAMPLE 60 6-(2,6-Dibromo-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine To a solution of 0.23 g 60% sodium hydride suspension in 11.0 mL of 2-ethoxyethanol was added 4.18 g of 2,6-dibromophenylacetonitrile and 2.00 g of 2,4-diaminopyrimidine-5-carboxaldehyde. The reaction was refluxed for 4 hours, cooled, and poured into ice water. The residue was washed well with acetonitrile then diethyl ether to give 3.62 g of 6-(2,6-dibromo-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine, CIMS (1% NH3 in CH4): 422=M+ +C2 H5, 396 (Base), 394=M+ +H, 393=M+; mp 284-289 C.

According to the analysis of related databases, 67197-53-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Blankley; Clifton John; Doherty; Annette Marian; Hamby; James Marino; Panek; Robert Lee; Schroeder; Mel Conrad; Showalter; Howard Daniel Hollis; Connolly; Cleo; US5733913; (1998); A;,
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Related Products of 51632-12-3, 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 51632-12-3 as follows.

1-1 (21.3 g, 89.6 mmol) is dissolved in DMF (300 mL). The mixture is cooled to 0 C and NaH (60% in oil suspension, 3.76 g, 94.1 mmol) is added slowly. The mixture is then stirred for a further 15 minutes and methyl iodide (5.9 mL, 94.1 mmol) is added. The reaction mixture is stirred at 0 C to room temperature for 2 hours and then concentrated in vacuo. The residue is partitioned between methylene chloride and brine. The combined organics are dried with Na2S04, filtered and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-15% EtOAc in hepatne) to give the title intermediate (21.7 g); m/z 252.3, 254.3 [M/M+2H].

According to the analysis of related databases, 51632-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John; LO, Ho Yin; LOKE, Pui Leng; LIU, Weimin; MORWICK, Tina Marie; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee; WO2012/24150; (2012); A1;,
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These common heterocyclic compound, 109305-98-8, name is 2-Bromo-4,5-dimethoxybenzonitrile, 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. COA of Formula: C9H8BrNO2

General procedure: S3 (1.5 mmol) was dissolved in NEt3 (5 mL) and degassed for 30 minutes at room temperature. Then PdCl2(PPh3)2 (0.2 mol%), CuI (0.2 mol%) and the alkyne were added to S3/NEt3 solution. The obtained dark brown suspension was stirred for 12 h at 60C. After cooling to room temperature the solvent of the reaction mixture was filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography (petroleum ether : ethyl acetate = 30:1) to provide 1t-1w (in 76-83% yield).

The synthetic route of 2-Bromo-4,5-dimethoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
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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. 133550-33-1, name is 2-Cyano-N-(3-phenylpropyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C12H14N2O

General procedure: To a stirred solution of N-alkyl-substituted 2-cyanoacetamide 1 (5mmol) in toluene (10 mL) was added NaN3 (3 equiv) and triethylamine hydrochloride salt (3 equiv). The reaction mixture was heated to 90 C for 20 h. Ice-cold H2O (25 mL) was added to the reaction mixture and acidified with aq HCl and stirred at 0 C for 30 min. The precipitated product was collected by filtration, washed with cold H2O(25 mL), and dried in vacuum (Table 1).

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 133550-33-1.

Reference:
Article; Wang, Yuanze; Patil, Pravin; Doemling, Alexander; Synthesis; vol. 48; 21; (2016); p. 3701 – 3712;,
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Related Products of 140860-51-1, 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 140860-51-1 as follows.

To a soln. of 2-bromo-4-methoxybenzonitrile (1 g,4.72 mmol )in MeCN (40 rnL) was added Nal (212 g, 14.15 mrnol ) and TMSC1 (1.54 g, 14.15 mmoi). Then the mixture was stirred at 80C overnight, Then the mixture was concentrated in. vacuo and poured into water basified with Na2CO3. The mixture was extracted with EtOAc. The aq. layer was acidified with HC1 and extracted with EtOAc. The organic layer was washed withbrine, dried (Na2SO4). and concentrated in vacuo to give the title compound.

According to the analysis of related databases, 140860-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADAMS, Gregory, L.; COX, Jason, M.; DEBENHAM, John, S.; EDMONDSON, Scott; GILBERT, Eric, J.; GUO, Yan; JIANG, Yu; JOSIEN, Hubert; KIM, Hyunjin, M.; LAN, Ping; MIAO, Shouwu; PLUMMER, Christopher, W.; RAJAGOPALAN, Murali; SHAH, Unmesh; SUN, Zhongxiang; TRUONG, Quang, T.; UJJAINWALLA, Feroze; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; SUZUKI, Takao; WANG, Nengxue; (182 pag.)WO2017/205193; (2017); A1;,
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Electric Literature of 133541-45-4, 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. 133541-45-4 name is 4-Bromo-2,5-difluorobenzonitrile, 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.

To a stirred suspension of 4-bromo-2,5-difluorobenzonitrile (91 g, 417 mmol) and potassium carbonate (173g, 1.25 mol) in N,N-dimethylformamide (910 ml) was added (S)-1,1,1-trifluoropropanol [CAS 3539-97-7] dropwise (52.4g, 460 mmol). The resulting mixture was heated at 70 C for for 15 hours and cooled to room temperature. The reactionwas concentrated and the residue was diluted with water. The aqueous solution was extracted with DCM (3x). Thecombined organic washes were washed with brine, dried over sodium sulfate, filtered, and concentrated under reducedpressure to give an oil (136.6 g). The residue was triturated with a mixture of hexanes and toluene (9:1, 200 mL) to givethe desired product as a white solid (90.3 g, 93% purity, 64% yield).LC-MS (Method A): Rt = 1.29 min; MS (ESIpos): m/z = 312.0 [M+H]+.1H-NMR (400 MHz, CHLOROFORM-d) delta [ppm]: 1.511 (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).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Bayer AG; Gradl, Stefan, Nikolaus; Niehues, Michael; Halfbrodt, Wolfgang; (43 pag.)EP3553052; (2019); A1;,
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57775-06-1, name is 2-(2-Bromophenyl)-2-methylpropanenitrile, 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-(2-Bromophenyl)-2-methylpropanenitrile

To a solution of 2-(2- bromophenyl)-2-methylpropanenitrile (4.0 g, 17.8 mmol), in dry THF (40 mL) was added borane-dimethyl sulfide (5.08 mL, 53.5 mmol) at 0 °C and the reaction mixture was slowly brought to rt, stirred for 1 h and then, heated to reflux for 18 h. The solvent was removed and quenched with MeOH, and heated to reflux for 18 h. The reaction was concentrated and the residue was dissolved in EtOAc, washed with H2O, brine, dried (Na2SO4), flltered and concentrated to give 4.0 g of 103 A as a white solid. MS (ESI) m/z: 230.2 (M+H)+.

The synthetic route of 57775-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; WO2013/56034; (2013); A1;,
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