Author: Jessica.F

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. 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, A new synthetic method of this compound is introduced below., name: 2,4,6-Trifluorobenzonitrile

NaH (60% in mineral oil, 1.21g, 30.3 mmol) was added in one portion to (E)-2-Buten-1-ol (1.62g, 20 mmol) in 20 ml THF with cooling from an ice water bath. The mixture was stirred for 10 min, then added dropwise to 2,4,6-trifluorobenzonitrile (3.2 g, 20 mmol) in 20ml THF, with cooling from an ice bath. The solution was stirred at room temperature for 4 hours, then quenched with acetic acid. This solution was dried onto silica gel and purified by normal phase chromatography using an ISCO Combiflash, eluted with ethyl acetate and hexane. Yield (3.2g, 80% yield). 1H NMR (300 MHz, CDCl3) delta 6.53(m, 2H) 5.93(m, 1H) 5.73(m, 1H) 4.60(m, 2H) 1.81(d, J=6Hz, 3H). LC/MS, 210.2 [M+H]+ calculated 210.2

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; CIDARA THERAPEUTICS, INC.; BALKOVEC, James, Michael; BENSEN, Daniel, C.; BORCHARDT, Allen; BRADY, Thomas, Patrick; CHEN, Zhi-yong; LAM, Thanh; TARI, Leslie, W.; (204 pag.)WO2016/201219; (2016); A1;,
Nitrile – Wikipedia,
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Application of 53312-80-4, 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. 53312-80-4, name is 4-Amino-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of tert-butyl 2-oxo-6-azaspiro[3.4]octane-6-carboxylate (CAS: 203661-716) (675 mg, 3.0 mmol), 4-amino-2-fluorobenzonitrile (408 mg, 3.0 mmol) and decaborane (128 mg, 1.05 mmol) in MeOH (10 mL) was stirred at 50 C overnight. After the reaction was completed, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Petroleum ether/EtOAc = 3/1) to afford intermediate 47 (500 mg, 48% yield) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-2-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
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Reference of 6011-14-9, 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 6011-14-9 as follows.

General procedure: For the aryl alpha-iminonitriles, a suspension of aminoacetonitrile hydrochloride (0.37 g, 4.0 mmol) and Et3N (1.0 mL, 7.2 mmol) in ethanol (10 mL) was stirred at room temperature for 0.5 h. To the resulting solution was added the corresponding aldehyde (2.0 mmol). After the reaction mixture was stirred for 1-2 h, the solvent was removed in vacuo. The residue was then diluted with EtOAc and washed with brine, dried over MgSO4, filtered and concentrated under in vacuo. The crude alpha-iminonitrile was used in next step without further purification.

According to the analysis of related databases, 6011-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jundong; Lin, Na; Yu, Lei; Zhang, Yandong; Tetrahedron Letters; vol. 57; 51; (2016); p. 5777 – 5780;,
Nitrile – Wikipedia,
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These common heterocyclic compound, 64695-82-5, name is 2-Bromo-4,5-difluorobenzonitrile, 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 2-Bromo-4,5-difluorobenzonitrile

2-Bromo-4,5-difluorobenzonitrile (1.0 g, 4.59 mmol), tert-butyl (2S)-2-methylpiperazine-1-carboxylate (0.96 g, 4.82 mmol), Pd2(dba)3 (0.21 g, 0.23 mmol), XantPhos (0.27 g, 0.46 mmol) and sodium tert-butoxide (1.32 g, 13.76 mmol) were suspended in 1,4-dioxane (20 ml) (degassed with nitrogen for 5 minutes) then the reaction was heated at 100 C. for 6 h. The reaction was cooled then filtered through Celite, using DCM. The filtrate was concentrated in vacuo then the residue was partitioned between DCM (50 ml) and water (30 ml) and the organics were separated, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash column chromatography using gradients of 0% to 100% EtOAc in heptane followed by 0% to 100% MeOH in EtOAc, then the fractions containing product were concentrated in vacuo to yield the title compound as a pale yellow oil which crystallized on standing (548 mg, 35%). 1H NMR (500 MHz, DMSO-d6) 8.04 (dd, J=10.4, 8.8 Hz, 1H), 7.32 (dd, J=12.7, 7.2 Hz, 1H), 4.24 (s, 1H), 3.84 (d, J=13.2 Hz, 1H), 3.32 (d, J=2.1 Hz, 2H), 3.16 (t, J=11.4 Hz, 1H), 2.90 (dd, J=12.1, 3.7 Hz, 1H), 2.78 (td, J=11.9, 3.4 Hz, 1H), 1.42 (s, 9H), 1.27 (d, J=6.7 Hz, 3H). LCMS Method 2-Tr=1.28 min (ES+) (M+H+) 360.1

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

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (519 pag.)US2018/127370; (2018); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 115279-73-7, name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, 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 115279-73-7, Product Details of 115279-73-7

A mixture of 2-chloronicotinoyl chloride (50 mg) and 1-(4-aminophenyl)-cyclopentanecarbonitrile (1 eq) and K2CO3 (80 mg) in dichloromethane (20 ml) was stirred at RT for 30 min. The reaction was filtered and the filtrate was evaporated. The residue was mixed with 6-aminoindazole (150 mg) neat and heated at 210 C. for 2 hour. The reaction was cooled and purified by column chromatography to give the title compound. Mass: (M+1), 423.

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; Chen, Guoqing P.; US2004/259916; (2004); A1;,
Nitrile – Wikipedia,
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These common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, 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. Recommanded Product: 33143-29-2

PREPARATION 8 2,2-Dimethyl-2H-1-benzopyran-6-carbonitrile (10 g) was dissolved in toluene (54 ml), and the solution was cooled to -78 C. under a nitrogen atmosphere, to this solution was added diisobutylaluminum hydride (1M solution in toluene, 81 ml) over 30 minutes, and the mixture was stirred at -78 C. for 10 minutes. The reaction mixture was quenched at -78 C. with ethyl acetate (54 ml) followed by 1M tartaric acid solution in water (100 ml). The cooling bath was removed and the mixture was vigorously stirred for 1 hour. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, and concentrated to give 2,2-dimethyl-2H-1-benzopyran-6-carbaldehyde (9.9 g) as a pale yellow oil, which was used without further purification. IR (Film): 1690, 1640 cm-1. NMR (CDCl3, delta): 1.47 (6H, s), 5.70 (1H, d, J=10Hz), 6.38 (1H, d, J=10Hz), 6.86 (1H, d, J=8Hz), 7.52 (1H, d, J=2Hz), 7.64 (1H, dd, J=2, 8Hz), 9.82 (1H, s).

The synthetic route of 2,2-Dimethyl-2H-chromene-6-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujisawa Pharmaceutical Company, Ltd.; US5104890; (1992); 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 4640-67-9 as follows. COA of Formula: C9H6FNO

1f (48.9mg, 0.3mmol), 1,2-dichloroethane (DCE, 1mL), 2-methyl-4-phenyl-3-butyne-2-ol (2a , 72.1mg, 0.45mmol),Dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer ([RhCp * Cl2] 2, 13.0mg, 0.021mmol) and CsOAc (57.6mg, 0.3mmol) will react in the air atmosphere The tube was sealed and the reaction was stirred at 100 C for 24 h. After the reaction, the reaction tube was cooled to room temperature, filtered with suction, and the mother liquor was mixed with silica gel and spin-dried, separated through a silica gel column (petroleum ether / ethyl acetate = 10/1) to obtain 3f (38.4 mg, 42%) as a yellow solid product.

According to the analysis of related databases, 4640-67-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Henan Normal University; Fan Xuesen; Song Xia; Zhang Xinying; (24 pag.)CN110746319; (2020); A;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 939-80-0, name is 4-Chloro-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 939-80-0, COA of Formula: C7H3ClN2O2

Example 1; Preparation of 4-(3,5-dimethylphenoxy)-3-(4-propionylpiperazin-l-ylsulfonyl)benzonitrile 57; [00201] Compound 57 was synthesized as shown in Scheme 2. Scheme 2 [00202] 4-(3,5-Dimethylphenoxy)-3-nitrobenzonitrile 21.; To a solution of 4-chloro-3- nitrobenzonitrile (12.00 g, 65.75 mmol) in THF was added potassium carbonate (45.58 g, 328.70 mmol) and 3,5-dimethylphenol (9.658 g, 78.88 mmol). The reaction mixture was refluxed for 17 hrs, whereupon the starting material was consumed (TLC, 25% EtOAc in hexanes). The reaction mixture was then cooled to room temperature, and potassium carbonate was filtered and washed with copious amounts of EtOAc. The filtrate was washed sequentially with saturated sodium bicarbonate solution, water, and saturated sodium chloride – 92 – SDI-13262vl solution, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give the crude product as a yellow solid. The solid was triturated with hexanes and filtered to afford compound 21 as a whitish-yellow powder. (15.022 g, 85.2% yield, 100 % HPLC purity). 1H NMR (500 MHz, DMSO-4): delta 8.65 (d, / = 2 Hz, IH), 8.06 (dd, J1 = 9 Hz, J2 = 2 Hz, IH), 7.12 (d, / = 9 Hz, IH), 6.97 (s, IH), 6.84 (s, 2H), 2.29 (s, 6H).

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

Reference:
Patent; AXIKIN PHARMACEUTICALS, INC.; LY, Tai, Wei; FORRESTER, Jared, Andrew; WO2010/123960; (2010); A2;,
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 21803-75-8 as follows. name: 4-Amino-3-chlorobenzonitrile

4-Amino-3-chloro-benzonitrile (100mg, 0.66mmol) and ICI (1.1eq, 0.72mmol, 117.05mg) was added. The reaction mixture was stirred for 12hrs. The reaction mixture was purified according to the similar procedure to step 2 of Example 40 to obtain 4-Amino-3-chloro-5-iodobenzonitrile (65.2mg, 35.80%). Mp: 121~123 C; IR( KBr pellet, cm-1): 3365, 2942, 2221,1634, 728; 1H NMR(400MHz, CDCl3): delta 7.42(d, 1 H, J=1.6Hz), 7.43(d, 1 H, J=1.6Hz), 5.01 (bs, 2H).

According to the analysis of related databases, 21803-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amorepacific Corporation; EP1862454; (2007); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, 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 21803-75-8, SDS of cas: 21803-75-8

To 3-chloro-4-amino-benzonitrile (5 g, 32.9 mmol) in Methanol (80 mL) was added dropwise bromine (5.3 g, 33.1 mmol) in Methanol (20 mL). The mixture was stirred for 1.5 hours. Solvent was removed by rotovap and resulting solid was dried in vacuum. 3-Chloro-4-amino-5-bromobenzonitrile was obtained as a white solid. 1H NMR (300 MHz, CD3OD): delta7.63 (s, 1H), 7.75 (s, 1H). MH+=230.97, 232.97.

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-Amino-3-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gerritz, Samuel; Shi, Shuhao; Zhu, Shirong; US2006/287287; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts