Month: June 2021

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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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. 874-97-5, name is 3-Cyanobenzyl alcohol, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Cyanobenzyl alcohol

NaH (28.8 mg, 60%, 0.72 mmol) was added to a solution of 7-chloro-1-methyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one (44 mg, 0.24 mmol) and 5-(hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile (71 mg, 0.242 mmol) in DMF (1.8 mL). The reaction mixture was stirred at rt for 30 min. Aqueous HCl solution was added to adjust pH to 7. Purification by Mass Directed AutoPrep (MDAP) afforded the title compound as a white solid (60 mg, 56% yield).

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; Glaxo Group Limited; Wan, Zehong; Long, Kai; Sang, Yingxia; Su, Xiaobo; US2014/179715; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1009-35-4, name is 4-Fluoro-3-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 1009-35-4, Recommanded Product: 4-Fluoro-3-nitrobenzonitrile

General procedure: Before each run, the system (see Fig.4) was allowed to equilibrate by pumping solvent through for 30min with the Tube-in-Tube device at 16bar of hydrogen. An omnifit cartridge (20.0mm OD, 15.0mm ID) containing 1g of Pd-C catalyst was used. To avoid an overpressure of the system in the event of blockage, the upper pressure cut-off limit on the Knauer pump was set to 25bar. With the injection loop disconnected from the flow line, the loop was opened and filled manually (using a syringe) with 3.6mL of a 0.076M solution of starting material in ethanol (excess starting material solution exiting the loop was recovered for reuse). The injection loop was then closed off and switched into the flow stream. The outlet from the system (downstream of the back-pressure regulator) was collected for 120min. The solvent was removed under reduced pressure (using a rotary evaporator followed by a 2-stage rotary vane pump) to afford the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Dimitriou, Eleni; Jones, Richard H.; Pritchard, Robin G.; Miller, Gavin J.; O’Brien, Matthew; Tetrahedron; vol. 74; 47; (2018); p. 6795 – 6803;,
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Electric Literature of 42872-73-1, 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. 42872-73-1, name is 2-Bromo-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

{4-methyl-2-[(propan-2-yl)amino]phenyl}(phenyl)methanaminium chloride – The titled compound was obtained following the modified procedure described in WO2006035157 (Protocol A). The starting material 2-(isopropylamino)-4- methylbenzonitrile was prepared from 2-bromo-4-methylbenzonitrile using a Ex.77 Buchwald-Hartwig reaction (2-bromo-4-methylbenzonitrile (1 eq.), isopropylamine (1 .5 eq.), BINAP (0.05 eq.), Pd2(dba)3 (0.03 eq.), Cs2C03 (2 eq.) in toluene at 90C for 6h) – Yield: 43% ; appearance: pale yellow solid ; 1 H NMR, d (ppm) (Methanol d4) : 1 .06 (d, 3H, J=6.2Hz); 1.15 (d, 3H, J=6.2Hz); 2.25 (s, 3H); 3.51 -3.58 (m, 1 H); 5.88 (s, 1 H); 6.61 (s, 2H); 7.25-7.47 (m, 6H); 8.94 (br s, 3H)

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

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; WALCZAK, Robert; MAJD, Zouher; PIHAN, Emilie; BONNET, Pascal; PERSPICACE, Enrico; (198 pag.)WO2016/102633; (2016); A1;,
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These common heterocyclic compound, 21667-62-9, name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, 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: 3-(3-Chlorophenyl)-3-oxopropanenitrile

To 3-chlorobenzoylacetonitrile (24,360 mg, 2 mmol) and sulfur (76 mg) in DMF (4 [N-IL),] triethylamine (0.25mL) is added under stirring. To this solution tetrahydro-4H-pyran-4-one (1,200 mg, 2 mmol) is added dropwise. The mixture is stirred for 16 hours and it is poured into water (30 [ML),] which is extracted with diethyl ether (30 [ML).] The ethereal solution is dried with sodium sulfate and concentrated to give the desired compound as an orange solid (253 mg, 43%). Physical characteristics: MS [(ES+)] for [M/Z] 294,296 (M+H).

The synthetic route of 3-(3-Chlorophenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/35591; (2004); 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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2

Synthesis of intermediate 13: 4~(4-Cyano- benzylcarbamoyl) -piperidine-1-carboxylic acid tert- butyl esterA solution of HOBt (1.54 g; 10 mmol) and TBTU (3.22 g; 10 mmol) in DMF (10ml) was added to a solution of N- Boc-piperidine-1-carboxylic acid (2 g; 8.72 mmol) and 4-cyanobenzylamine (8.72 mmol) in DMF (10 ml) followed by TEA (4.85 ml; 35 mmol). After 16h, water was added to the reaction mixture and the mixture was extracted with DCM (3 times) . The combined organics were washed with an aqueous solution of NaHCO3 and water and dried (MgSO4) . The residue was purified by silica gel chromatography (eluent:DCM and MeOH/DCM: 5/95) to afford after dry evaporation the title intermediate as an oil (2.4g; Y:80%) .MS: (M+H)+ = 344.

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 10406-25-4.

Reference:
Patent; EUROSCREEN S.A.; WO2009/10480; (2009); A1;,
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Reference of 53312-81-5, These common heterocyclic compound, 53312-81-5, name is 5-Amino-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.

Lithium bis(trimethylsilyl)amide in toluene (0.59 mL, 1 M, 0.59 mmol) was added to ethyl 3 -fluoro- 1 -methyl-4-[ [1 -(trifluoromethyl)cyclopentyl]sulfamoyl] pyrrole-2-carboxylate (57 mg, 0.148 mmol) and 5-amino-2-fluoro-benzonitrile (26.1 mg, 0.19 mmol) in THF (10 mL) at room temperature under nitrogen. The reaction mixture was stirred 1 hour, quenched with NH4C1(25 mL) solution, diluted with brine (25 mL) and extracted with EtOAc (50 mL). The organic layer was dried over magnesium sulphate, filtered and concentrated. The residue was purified by silica gel column chromatography using a gradient from 10 to 100% EtOAc in heptane. The product fractions were concentrated. The residue was dissolved in hot methanol (10 mL). The product crystallised upon addition of water. Compound 281 (30.5 mg) was filtered off and driedovernight in vacuo at 50C. Method D: Rt: 2.02 mm mlz: 475.3 (M-H) Exact mass: 476.1. ?HNMR (400 MHz, DMSO-d6) oe ppm 1.42 – 1.54 (m, 2 H), 1.58 – 1.71 (m, 2 H), 1.72 – 1.85 (m, 2H), 2.21 – 2.32 (m, 2 H), 3.81 (s, 3 H), 7.50 – 7.57 (m, 2 H), 7.97 (ddd, J=9.2, 4.8, 2.9 Hz, 1 H),8.17 (dd, J=5.8, 2.8 Hz, 1 H), 8.32 (s, 1 H), 10.33 (s, 1 H). Differential scanning calorimetry:From 30 to 300 C at 10C/mm: peak at 187.0 C.

The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 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 103146-25-4, Product Details of 103146-25-4

To a stirred solution [OF RACEMIC 4- [4-DIMETHYLAMINO-1- (4-FLUORO-PHENYL)-1-HYDROXY-] [BUTYL]-3-HYDROXYMETHYL-BENZONITRILE] (0,29 mmol, 100 mg) and vinylbutyrate (0,29 mmol, [37 L)] in anhydrous toluene (2,925 ml) is added Novozymes 435, (0,2 mg) and 1,1 eq. Carboxylic acid. The reaction is heated to 40 degrees celcius and followed by HPLC. The enzyme is filtered off and washed with a small amount of toluene. The combined organic phases are evaporated in vacuo and subsequently analyzed on super critical fluid chromatography. Result is shown in table 19.

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; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17417-09-3, name is 2-Fluoro-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 17417-09-3, Recommanded Product: 17417-09-3

Ethyl 3-amino-5-nitrobenzothiophene-2-carboxylate. 2-Fluoro-5-nitrobenzonitrile (1.664 g, 10 mmol), ethyl thioglycollate (1.21 g, 10 mmol) and NEt3 (3.06 g, 30 mmol) are stirred in DMSO (5 mL) at 100 C. under N2 for h h. The deep orange-red reaction mixture is poured onto ice-water (50 mL), and the solid is collected by suction filtration, rinsed with water, and dried in a vacuum oven at 60 C. to give ethyl 3-amino-5-nitrobenzothiophene-2-carboxylate (2.675 g, 100%) as a bright orange solid. 1 H NMR (DMSO) delta9.23 (1H, d, J=2.1 Hz), 8.28 (1H, dd, J=2.3, 8.9 Hz), 8.10 (1H, d, J=9.0 Hz), 7.45 (2H, brs), 4.29 (2H, q, J=7.1 Hz), 1.30 (3H, t, J=7.1 Hz).

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

Reference:
Patent; Warner-Lambert Company; US5679683; (1997); A;,
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Application of 50594-78-0, These common heterocyclic compound, 50594-78-0, name is 5-Fluoro-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.

5-(4-Methylpiperazinyl)-2-nitrobenzenecarbonitrile 5-Fluoro-2-nitrobenzenecarbonitrile (1.02 eq) and N-methylpiperazine (1.0 eq) were dissolved in NMP. Triethylamine (2.1 eq) was added, and the resulting solution heated at 100 C. for 1 hour. The solution was cooled to room temperature and poured into H2O. A precipitate formed which was filtered to yield the desired product as a green solid. LC/MS m/z 247.3 (MH+), Rt 1.46 minutes.

Statistics shows that 5-Fluoro-2-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 50594-78-0.

Reference:
Patent; Chiron Coporation; US2003/28018; (2003); A1;; ; Patent; Renhowe, Paul A.; Pecchi, Sabina; Machajewski, Timothy D.; Shafer, Cynthia M.; Taylor, Clarke; McCrea JR., William R.; McBride, Christopher; Jazan, Elisa; US2002/107392; (2002); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts