Month: September 2021

Application of 261951-81-9, 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. 261951-81-9, name is 3-Fluoro-2-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 3-fluoro-2- (trifluoromethyl)benzonitrile g, 6.3 mmol) and piperazine (0.72 g, 8,4 mmol) in acetonitrile (6 ml) was heated under microwave radiation at 150 C for 15 minutes. The reaction mixture was poured into water (50 ml) and the aqueous phase was extracted with ethylacetate (3×50 ml). The combined organic phases was dried (MgS04), filtered and evaporated to dryness. Purification by flash column chromatography (ethylacetate/methanol, 1:1) gave the title compound: 1.1 g. MS m/z (rel. intensity, 70 eV) 255 (M+, 16), 214 (11), 213 (bp), 171 (8), 151 (7).

The synthetic route of 3-Fluoro-2-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; A. CARLSSON RESEARCH AB; WO2005/121087; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, 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. Quality Control of 4-Bromo-2-fluoro-3-methylbenzonitrile

General procedure: A mixture of 4-bromo-2-fluoro-3-methylbenzonitrile (7.00 g, 32.7mmol), potassium vinyltrifluoroborate (5.3 g, 39 mmol) and Pd(dppf)Cl2 (0.5 g, 0.7 mmol) in 70 mL of EtOH and 30mL of TEA was refluxed under Ar for 4 hours. Concentrated, the residue was purified by column chromatography(petrol ether: EtOAc = 10 :1) to afford 4-ethenyl-2-fluoro-3-methylbenzonitrile.

The synthetic route of 4-Bromo-2-fluoro-3-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; (128 pag.)EP2744499; (2016); B1;,
Nitrile – Wikipedia,
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Electric Literature of 5866-98-8, 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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,6-dichloro-3-nitrobenzonitrile (750.0 g, 3.45 mol, 1.0 equiv.) in ethanol (7.5 L, 10.0 V) at 15-20 C. was slowly added hydrazine hydrate (519.0 g, 10.36 mol, 3.0 equiv.) while maintaining the reaction mass below 25 C (Observation: Addition is slightly exothermic and solid formation will begin upon addition). The reaction mixture temperature was slowly raised to room temperature and then the mixture was stirred for 3 h (Observation: the quantity of solids will increase during this time). After completion of the reaction (monitored by TLC), the mixture was diluted with water (7.5 L, 10.0 V) and further stirred for 1 h at room temperature. The solids were isolated via filtration and then were washed with water (2.25 L, 3.0 V). The wet solid was washed with a 1 : 1 ratio mixture of acetone (1.875 L, 2.5 V) and hexanes (1.875 L, 2.5 V). Bulk residual water was removed from the solids by maintaining vacuum filtration for 60-90 min. The wet solid was finally dried in a hot air oven for 7-8 h at 50 C (until moisture content reaches below 1.5%) to get the dried product, 4-chloro-7-nitro-li/-indazol-3 -amine (549.0 g, 75% yield) as a brick red- colored solid. NMR (400 MHz, CDCL): d 10.36 (bs, 1H), 8.20 (d, J= 8.4 Hz, 1H), 7.07 (d, J= 8.40 Hz, 1H), 4.73 (bs, 2H).

The chemical industry reduces the impact on the environment during synthesis 2,6-Dichloro-3-nitrobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; IWUAGWU, Christiana; PEESE, Kevin M.; (0 pag.)WO2020/58844; (2020); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 115279-73-7, 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 115279-73-7 as follows.

To a solution of 4-hydroxy-3-methoxy-benzoic acid (90.0 mg; 0.54 mmol) in DCM (1.8 mL) were added few drops of DMF. Oxalyl chloride (180 uL; 2.12 mmol) was added dropwise to this solution, which then was stirred at room temperature for 16 hours. The solvent was evaporated under vacuum and the resulting yellow oil was dissolved in DCM (5.52 mL). This solution was added dropwise to a stirred mixture of l-(4-amino-phenyl)-cyclopentanecarbonitrile (100 mg; 0.54 mmol), prepared as in 3(B), and triethylamine (150 uL; 1.07 mmol) in DCM (4.6 mL). After stirring at room temperature for 3 hours, the solvent was evaporated under vacuum. The product was purified by preparative HPLC (Method Q), to yield the titled compound as a yellow oil (20.0 mg; 11% yield).1H NMR (300 MHz, CDC13) delta(ppm): 7.83 (br. s., 1 H), 7.64 (m, 2 H), 7.53 (d, 1 H), 7.43-7.50 (m, 2 H), 7.34 (dd, 1 H), 7.00 (d, 1 H), 3.99 (s, 3 H), 2.40-2.56 (m, 2 H), 1.84-2.17 (m, 6 H). LCMS (RT): 2.76 min (Method H); MS (ES+) gave m/z: 337.1 (MH+).

According to the analysis of related databases, 115279-73-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 198633-76-0, 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. 198633-76-0, name is 2-Fluoro-6-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Fluoro-6-methyl- benzonitrile (1000 mg, 7.4 mmol) was added to trifluoromethanesulfonic acid (4.98 mL, 56.2 mmol) cooled in ice. The resulting cold solution was treated with N-bromosuccinimide (1380 mg, 7.8 mmol). The mixture was allowed to stir at ambient temperature. After 30 min, the reaction mixture was poured into ice water and extracted with 2 portions dichloromethane. The combined dichloromethane layers were washed with brine, dried over MgS04, filtered, and evaporated to yield 3-bromo-6-fluoro-2-methyl-benzonitrile (1560 mg, 7.3 mmol, 98% yield) as a light brown oil that solidified.

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-Fluoro-6-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; DIXON, Darryl, David; GRINA, Jonas; JOSEY, John, A.; RIZZI, James, P.; SCHLACHTER, Stephen, T.; WALLACE, Eli, M.; WANG, Bin; WEHN, Paul; XU, Rui; YANG, Hanbiao; WO2015/35223; (2015); A1;,
Nitrile – Wikipedia,
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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 6306-60-1 as follows. Product Details of 6306-60-1

EXAMPLE IV A mixture of 18.5 parts of 2,4-dichlorobenzeneacetonitrile and 180 parts of N,N-dimethylformamide is stirred and cooled in an ice-bath while nitrogen gas is introduced. 3.2 Parts of a sodium hydroxide solution 78% are added portionwise and the whole is stirred for one hour. Then there are added dropwise, during a one hour-period, 17.8 parts of (bromomethyl)cyclohexane while still cooling and while nitrogen gas is still introduced. Upon completion, stirring is continued for 2 hours at room temperature. The reaction mixture is poured onto water. The precipitated product is filtered off and triturated in a mixture of methanol and water. The product is filtered off and dried, yielding 25.5 parts of 2,4-dichloro-alpha-(cyclohexylmethyl)benzeneacetonitrile; mp. 58.8 C.

According to the analysis of related databases, 6306-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4598085; (1986); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 218632-01-0,Some common heterocyclic compound, 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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.

te^-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2-nitrophenylamino)-8-oxo-8,9- dihydropurine-7-carboxyIate (58). Sodium hydride (88 mg, 95%) was added, under argon flush, to a solution of tert-bntyl 9-(2,6-difluorobenzyl)-2-amino-8-oxo-8,9- dihydropurine-7-carboxylate (57) (191 mg) and 3-fluoro-4-nitrobenzonitrile (415 mg) in DMF (5 mL) at -40 C. The reaction mixture was allowed to warm to -20 0C over 3 hr then quenched by the addition of sat. aq. NH4Cl, once at RT the mixture was diluted with EtOAc and separated. The organics were washed with brine (3 x), dried, filtered and evaporated, purified via column chromatography, (eluted with DCM and 1 and 2.5 % MeOH/DCM) to yield tert-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2- nitrophenylamino)-8-oxo-8,9-dihydropurine-7-carboxylate (58) (288 mg), MH+ = 524.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluoro-4-nitrobenzonitrile, its application will become more common.

Reference:
Patent; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/108103; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, 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 499983-13-0, Formula: C8H5BrFN

A solution of 4-bromo-3-fluorophenylacetonitrile (Ig, 4.6 mmoles) in toluene (4 ml) is added with 0.6 ml (7 mmoles) of 1,2-dibromoethane, a 50% NaOH aqueous solution (4 ml) and tetrabutylammonium bromide (0.32 g, 1 mmoles). The mixture is kept under stirring at room temperature for 4 hours, then diluted with water and extracted with ethyl acetate. The organic phase is recovered and solvent is eliminated under vacuum to give a brown solid, which is subjected to silica gel chromatography purification, to afford an orange to yellow product in the solid form (I g, yield 90%).

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

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; PIVETTI, Fausto; FORNARETTO, Maria Gioia; RE, Marco; WO2011/15287; (2011); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 94087-40-8, name is 3-Chloro-2-fluorobenzonitrile, 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: C7H3ClFN

General procedure: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

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

Reference:
Article; Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela; Tetrahedron Letters; vol. 53; 20; (2012); p. 2548 – 2551;,
Nitrile – Wikipedia,
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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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H12N2

A mixture of compound 3 (6.75g, 0.0215mol) and 2-(4-aminophenyl)-2-methylpropanenitrile (compound 4, 3.72g, 0.0233mol) in 2-propanol (25ml) was heated at reflux for 30min. The precipitated solid was collected and dried to give ethyl 6-bromo-4-(4-(2-cyanopropan-2-yl)phenylamino)quinoline-3-carboxylate (compound 5, 8.35g, 88.9%) as a bright yellow solid.

According to the analysis of related databases, 115279-57-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADVENCHEN PHARMACEUTICALS, LLC; GUOQING, Paul, Chen; CHANGREN, Yan; MONICA, Chen; (33 pag.)WO2017/11363; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts