Category: 1009-35-4

Reference of 1009-35-4, 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 1009-35-4 as follows.

To a suspension of sodium hydride (60’Yo, 0.58 g) in THF (2 ml), wasadded 4-fluoro-3-nitro-benzonitrile (1.33 g, 8.0 rnmol) and 2-arnino-5-methylthiophene-3-carbonitrile (1. i 0 g, 8.0 rnmol) in THF (1 0 ml), dropwise. The mixture was stirred at room temperature overnight. Two more batches of sodium hydride(60percent, 0.50 g and OA g) were added over the next 6 hours. After stirring for 3 days,the mixture was poured into ice-water (20 ml) and acidified to pH 3 with 6Nhydrochloric acid (7 ml). The precipitate was filtered and washed with water. Thesolid was extracted with dichloromethane (35 ml). The solution was concentrated toa solid, and used in the next step without additional purification. LC-MS: rn/z 285(M+1 ), 307 (M+23). 1H NMR (CDCb, 400 MHz): i5 (ppm) 9.76 (s, 1 H), 8.59 (s, 1 H),7.70 (d, 1H), 7.14 (d, 1H), 6.87 (s, 1H), 2.52 (s, 1H).

According to the analysis of related databases, 1009-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORTHO-CLINICAL DIAGNOSTICS, INC; JANSSEN PHARMACEUTICA NV; HRYHORENKO, Eric; SANKARAN, Banumathi; DECORY, Thomas, R.; TUBBS, Theresa; COLT, Linda; REMMERIE, Bart, M.; SALTER, Rhys; DONAHUE, Matthew, Garrett; GONG, Yong; WO2014/31656; (2014); 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 1009-35-4 as follows. Quality Control of 4-Fluoro-3-nitrobenzonitrile

10623] To a stirred solution of 4-fluoro-3-nitrobenzonitrile (1 g, 6.02 mmol) in CH2C12 (5 mE) was added potassium carbonate (1.66 g, 12.05 mmol) followed by cyclopropanamine (3.33 mE, 48.19 mmol) dropwise at 0¡ã C. under an inert atmosphere. The reaction mixture was gradually warmed to room temperature and stirred for 4 h. After consumption of starting material (by TEC), the reaction mixture was poured into water (30 mE) and extracted with EtOAc (2×50 mE). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 4-(cyclopropylamino)-3-ni- trobenzonitrile (1.1 g) as a yellow solid. The crude material was taken to the next step without further purification.10624] ?H NMR (400 MHz, CDC13): oe 8.49 (d, J=1.9 Hz,1H), 8.41 (brs, 1H), 7.66-7.63 (m, 1H), 7.40 (d, J=9.0 Hz,1H), 2.68-2.61 (m, 1H), 1.04-0.98 (m, 2H), 0.75-0.70 (m,2H)10625] EC-MS: m/z 202.0 [M?H] at 2.88 RT (99.48percent purity)

According to the analysis of related databases, 1009-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; Hoekstra, William J.; (156 pag.)US2018/185362; (2018); A1;,
Nitrile – Wikipedia,
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These common heterocyclic compound, 1009-35-4, name is 4-Fluoro-3-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. SDS of cas: 1009-35-4

To a flask charged with 4-fluoro-3-nitrobenzonitrile (0.984 g, 5.92 mmol) in ACN (19.75 mL), was added trans-n-boc- 1 ,4-cyclohexanediamine (1.269 g, 5.92 mmol) and TEA (1.651 mL, 1 1.85 mmol). The resulting mixture was stirred at 80¡ãC for 3 h leading to complete conversion. The mixture was cooled to RT. The resulting solid was filtered, washed with water and dried to give tert-butyl ((lr,4r)-4-((4- cyano-2-nitrophenyl) amino)cyclohexyl)carbamate (1.93 g, 5.36 mmol, 90 percent yield) as yellow solid, which was used for next step without further purification. lH NMR (400 MHz, DMSO-i/6) delta ppm 8.29 – 8.37 (m, 1 H) 7.96 – 8.10 (m, 1 H) 7.53 – 7.71 (m, 1 H) 7.13 (d, J=9.29 Hz, 1 H) 6.64 (d, J=7.82 Hz, 1 H) 3.34 – 3.62 (m, 1 H) 3.09 (d, J=2.25 Hz, 1 H) 1.81 (d, J=10.27 Hz, 2 H) 1.65 (d, J=10.47 Hz, 2 H) 1.09 – 1.38 (m, 13 H). m/z (ESI) 361.2

The synthetic route of 4-Fluoro-3-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John L.; CHAKKA, Nagasree; DIMAURO, Erin F.; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Xin; WO2014/36022; (2014); A1;,
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Application of 1009-35-4, 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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

4-fluoro-3-nitrobenzonitrile (5 g, 30 mmol) is first of all subjected to catalytic hydrogenation with 5% palladium on activated charcoal (0.4 g) in 300 mL methanol (2 h at 2 bar hydrogen pressure), whereupon the 3-amino-4-fluorobenzonitrile formed is obtained as a solid after filtration and evaporation of the solvent. Yield: 4.1 g.

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-3-nitrobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MCCONNELL, Darryl; BETZEMEIER, Bodo; GERSTBERGER, Thomas; IMPAGNATIELLO, Maria; STEURER, Steffen; van der VEEN, Lars; WEYER-CZERNILOFSKY, Ulrike; US2008/81802; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H3FN2O2

A mixture of 4-fluoro-3-nitrobenzonitrile (5.0 g, 30.1 mmol) and Fe powder (5.05 g, 90.3 mmol) in AcOH (100 mL) was heated at 80¡ã C. for 1 hour under N2. Then the solvent was removed under vacuum and water (200 mL) was added to the residue. The solution was adjusted to pH 6 by addition of Na2CO3?and extracted with DCM (2¡Á200 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated to yield 3-amino-4-fluorobenzonitrile (48), which was used without further purification. MS m/z 137.0 (M+1)+.; To a stirring suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (1) (3.0 g, 18.5 mmol) in anhydrous dichloromethane (50 mL) at 0¡ã C. was added dropwise oxalyl chloride (4.84 mL, 55.5 mmol). Then, three drops of anhydrous DMF was added and the reaction mixture was stirred at room temperature for 15 minutes. The solvent was concentrated and the crude solid was added to a stirring solution of 3-amino-4-fluorobenzonitrile (48) (2.5 g, 18.5 mmol) in anhydrous pyridine (50 mL) at room temperature. The reaction was stirred for 20 minutes and quenched with water (200 mL) with stirring for another 10 minutes. Then the precipitate was filtered and dried in air to yield N-(5-cyano-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (49).?1H NMR (400 MHz, d6-DMSO) delta 10.40 (s, 1H), 9.43 (td, J=1.2, 6.8 Hz, 1H), 8.63 (s, 1H), 8.21 (dd, J=2.0, 7.2 Hz, 1H), 7.78-7.84 (m, 2H), 7.54-7.63 (m, 2H), 7.22 (dt, J=1.2, 6.8, 1H). MS m/z 281.1 (M+1)+.; NH2OH (10 mL, 32.1 mmol) was added in one portion to a stirred suspension of N-(5-cyano-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (49) (3.6 g, 12.85 mmol) in EtOH (100 mL). The resulting suspension was heated at 70¡ã C. for 3 hours and then the solvent was removed to yield N-(2-fluoro-5-(N?-hydroxycarbamimidoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (50).?1H NMR (400 MHz, d6-DMSO) delta 10.21 (s, 1H), 9.70 (s, 1H), 9.45 (td, J=1.2, 7.2 Hz, 1H), 8.61 (s, 1H), 7.95 (dd, J=2.4, 7.6 Hz, 1H), 7.79 (td, J=1.2, 8.8 Hz, 1H), 7.51-7.60 (m, 2H), 7.31-7.37 (m, 1H), 7.19 (dt, J=1.2, 6.8, 1H), 5.88 (s, 2H). MS m/z 314.1 (M+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 1009-35-4.

Reference:
Patent; IRM LLC; YEH, Vince; LI, Xiaolin; LIU, Xiaodong; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; US2013/59846; (2013); A1;,
Nitrile – Wikipedia,
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Electric Literature of 1009-35-4, The chemical industry reduces the impact on the environment during synthesis 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

A mixture of 4-fluoro-3-nitrobenzonitrile (5.0 g, 30.1 mmol) and Fe powder (5.05 g, 90.3 mmol) in AcOH (100 mL) was heated at 80 C for 1 hour under N2. Then the solvent was removed under vacuum and water (200 mL) was added to the residue. The solution was adjusted to pH 6 by addition of Na2C03 and extracted with DCM (2 x 200 mL). The organic layers were combined, dried over Na2S04, filtered and concentrated to yield 3- amino-4-fluorobenzonitrile (48), which was used without further purification. MS m/z 137.0 (M+1 ) +. To a stirring suspension of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (3.0 g, 18.5 mmol) in anhydrous dichloromethane (50 mL) at 0 C was added dropwise oxalyl chloride (4.84 mL, 55.5 mmol). Then, three drops of anhydrous DMF was added and the reaction mixture was stirred at room temperature for 15 minutes. The solvent was concentrated and the crude solid was added to a stirring solution of 3-amino-4- fluorobenzonitrile (48) (2.5 g, 18.5 mmol) in anhydrous pyridine (50 mL) at room temperature. The reaction was stirred for 20 minutes and quenched with water (200 mL) with stirring for another 10 minutes. Then the precipitate was filtered and dried in air to yield N-(5-cyano-2-fluorophenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (49). 1 H NMR (400MHz, c/6-DMSO) delta 10.40 (s, 1 H), 9.43 (td, J = 1 .2, 6.8 Hz, 1 H), 8.63 (s, 1 H), 8.21(dd, J = 2.0, 7.2 Hz, 1 H), 7.78-7.84 (m , 2H), 7.54-7.63 (m , 2H), 7.22 (dt, J = 1 .2, 6.8, 1 H). MS m/z 281 .1 (M+1 ) +. NH2OH (10 mL, 32.1 mmol) was added in one portion to a stirred suspension of N-(5- cyano-2-fluorophenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (49) (3.6 g, 12.85 mmol) in EtOH (100 mL). The resulting suspension was heated at 70 C for 3 hours and then the solvent was removed to yield N-(2-fluoro-5-(N’- hydroxycarbamimidoyl)phenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (50). 1 H NMR (400MHz, c/6-DMSO) delta 10.21 (s, 1 H), 9.70 (s, 1 H), 9.45 (td, J = 1 .2, 7.2 Hz, 1 H), 8.61 (s, 1 H), 7.95 (dd, J = 2.4, 7.6 Hz, 1 H), 7.79 (td, J = 1 .2, 8.8 Hz, 1 H), 7.51 -7.60 (m , 2H), 7.31 -7.37 (m, 1 H), 7.19 (dt, J = 1 .2, 6.8, 1 H), 5.88 (s, 2H). MS m/z 314.1 (M+1 ) +.

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-Fluoro-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3FN2O2

[0224] To a solution of 4-fluoro-3-nitrobenzonitrile (74.1 mg, 0.446 mmol) and l-(thiophen-2- yimethyl)piperazine (0.081 g, 0.446 mmol) in ACN (1 mL) was added K2CO3 (0.185 g, 1.338 mmol) The reaction mixture was heated to 80¡ãC for 3 hours and then diluted with water (3 mL). The liquid phase was decanted and the solid phase was washed with water and dried in a vacuum oven at 70¡ãC for 4 hours to give the title compound, which was used without further purification.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H3FN2O2

EXAMPLE 66(R)-trans-1-carbamoyl-4-adamantyl 3-(5-cyano-2-oxo-2,3-dihydro-1 H- benzo[d]imidazol-1 -yl)pyrrolidine-1 -carboxylateStep 1; A mixture of (R)-1-(methoxycarbonyl)adamantan-4-yl 3-aminopyrrolidine-1- carboxylate HCI salt (166 mg, 0.46 mmol), prepared as described in WO 2009/131669, 4-fluoro-3-nitrobenzonitrile (1 15 mg, 0.69 mmol), i-Pr2NEt (0.25 ml_, 1.4 mmol) and n-PrOH (3 ml.) was heated at 120 0C for 1 h in the microwave. The mixture was diluted with EtOAc (100 ml_), washed with water (10 ml_), 2percent aq HCI (10 ml.) and brine (10 ml_), and dried over Na2SO4. Removal of the solvent left an orange oil (293 mg) which was purified by prep HPLC to afford (R)-1- (methoxycarbonyl)adamantan-4-yl 3-((4-cyano-2-nitrophenyl)amino)pyrrolidine-1- carboxylate (80 mg, 37percent) as a yellow oil. LC-MS Method 1 tR = 1.93 min, m/z = 469.

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; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; LEFTHERIS, Katerina; SINGH, Suresh, B.; TICE, Colin, M.; YE, Yuanjie; ZHUANG, Linghang; WO2010/141424; (2010); 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, COA of Formula: C7H3FN2O2

N-(4-Cvano-2-nitrophenyl)-N-methylglycineA mixture of 4-fluoro-3-nitrobenzonitrile (3.0 g) and sarcosine (2.53 g) with sodium hydrogen carbonate (2.39 g) in water (15 mL) and ethanol (15 mL) was heated at 8O0C. After 2 hours, the reaction was concentrated to half its volume and poured into IM HCl (50 mL). The aqueous solution was extracted with ethyl acetate and then with chloroform. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The residue was suspended in a minimum of dichloromethane and filtered yielding 3.74 g of product.MS TES): 236 (MH+) for Ci0H9N3O41H NMR (DMSO-D^ delta: 2.87 (s, 3H); 4.19 (s, 2H); 7.13 (d, IH); 7.82 (dd, IH); 8.29 (d,IH); 13.03 (s,lH).

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:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/71981; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts