Month: March 2021

Synthetic Route of 127510-96-7,Some common heterocyclic compound, 127510-96-7, name is Methyl 2-cyano-4-fluorobenzoate, molecular formula is C9H6FNO2, 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.

Step 1: 5-(3-(3-(3-((1r,3r)-3-((5-(5H-pyrido[4,3-b]indol-7-yl)-3-(trifluoromethyl)pyridin-2-yl)oxy)cyclobutoxy)propoxy)propoxy)azetidin-1-yl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione A mixture of 7-(6-((1r,3r)-3-(3-(3-(azetidin-3-yloxy)propoxy)propoxy)cyclobutoxy)pyridin-3-yl)-5-methyl-5H-pyrido[4,3-b]indole (crude, 0.390 mmol) [prepared as described for Compound 104], N-ethyl-N-isopropylpropan-2-amine (86 mg, 1.17 mmol) and methyl 2-cyano-4-fluorobenzoate (90 mg, 0.468 mmol) in 1-methyl-2-pyrrolidinone (3 ml) was stirred at 90 C. for 16 hour. TLC showed the reaction was complete. The reaction mixture was partitioned between ethyl acetate (20 ml) and water (30 ml). The organic layer was collected, washed with brine (20 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude residue which was purified by silica gel flash column chromatography (eluted with 2-4% methanol in dichloromethane) to afford 5-(3-(3-(3-((1r,3r)-3-((5-(5H-pyrido[4,3-b]indol-7-yl)-3-(trifluoromethyl)pyridin-2-yl)oxy)cyclobutoxy)propoxy)propoxy)azetidin-1-yl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (160 mg, yield 61%) as light yellow oil.

The synthetic route of 127510-96-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H5F3N2

Step 2: 4- [2, 5-Dioxo-3-methyl-4-phenylimidazolidin-l-yl]-2-trifluoromethyl-benzonitrile; [00272] To a solution of 1.26 g of triphosgene in 20 mL of anhydrous toluene is added slowly a solution of 1.18 g of 4-amino-2-trifluoromethylbenzonitrile in 16 mL of anhydrous dioxan. The mixture is refluxed for 1.5 hour. After cooling at rt the mixture is evaporated to dryness. To this crude product diluted with 50 mL of anhydrous THF is added 1.13 g of methyl 2-methylamino-2-phenylacetate in 10 mL of THF. The mixture is stirred at rt for 30 min. 1.96 mL of TEA is added, the mixture is refluxed for 1.5 hour and stirred at rt for 16 h then evaporated to dryness. The crude product is diluted with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic phases are washed wiith water then brine, and dried over magnesium sulfate, filtered and evaporated. The crude product is crystallised in ethyl acetate, filtered and rinsed with ethyl ether to provide the desired product.TLC: Fr = 0.67 (dichloromethan/ethyl ether 90/10) delta 1H NMR (CDCl3): 3.06 (s, 3H); 5.06 (s, IH); 7.35-7.39 (m, 2H); 7.48-7.56 (m, 3H); 7.96 (d, IH); 8.03 (dd,IH); 8.18 (d, IH)LCMS : (rt = 2.91min, apolar method): not ionizable

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; NIQUE, Francois; JAGERSCHMIDT, Catherine; BLANQUE, Roland; LEFRANCOIS, Jean-Michel; PEIXOTO, Christophe; DEPREZ, Pierre; TRIBALLEAU, Nicolas; WIGERINCK, Piet, Tom, Bert, Paul; NAMOUR, Florence, Sylvie; WO2010/29119; (2010); A1;,
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Electric Literature of 3218-45-9, 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. 3218-45-9 name is 2-(2,3-Dichlorophenyl)acetonitrile, 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 suspension of 2,3-dichiorophenyiacetonitriie {45 kg, 241 .9 mole) in methanol litres) was charged 30% w/w sodium methoxide in methanol solution ( 1 13.5 kg, 630.6 mole) then ethyifluoroacetate (29.7 kg, 280.1 mole). The reaction mixture was stirred overni¡ãhi and the product was precipitated from aqueous hydrochloric acid (63.7 kg, 648 mole) in water (350 litres). The slurry was filtered and the solid was dissolved in ethyl acetate and washed with brine solution. Ethyl acetate (100 litres) was removed by vacuum distillation. DMF (70 litres) was added and the distillation continued to remove the remaining ethyl acetate.To the resulting enol in DMF was added potassium carbonate (20 kg. 145 mole) over a period of 10 minutes. Aikyiation of the potassium enoiale was achieved using ethyl iodide (37.7kg, 24^ .9 mole) at 70’C for VA hours. The reaction mixture was partitioned between toluene (140 litres) and water (75 litres) and the toluene chase was washed with water (50 litres). Toluene (75 iitres) was removed by distillation to afford the crude product as a toluene solution.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2,3-Dichlorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/93587; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 57381-51-8, The chemical industry reduces the impact on the environment during synthesis 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

c 2-[3-Amino-1-(2-oxazolyl)propoxy]-4-chlorobenzonitrile oxalate To a solution of the product from Example 56(b) (160 mg) in dimethylformamide (2 ml) was added sodium hydride (76 mg of a 60% dispersion in mineral oil) and the reaction stirred for 1 h. Solid 4-chloro-2-fluoro-benzonitrile (296 mg) was added and the reaction stirred for 2 h. Water was added and the solution extracted with diethyl ether. The organic extract was separated, dried (sodium sulphate) and the solvent removed in vacuo. The residue was taken up in tetrahydrofuran (4 ml) and triphenylphosphine (283 mg) added. After 5 minutes, water (1 ml) was added and the reaction stirred for 16 h. Further water (2 ml) was added and the reaction stirred at 55 C. for 3 h and then 48 h at room temperature. The reaction was poured into ethyl acetate/aqueous 1N sodium hydroxide. The organic extract was separated, dried (sodium sulphate) and the solvent removed in vacuo. Purification by RP-HPLC afforded the free base of the title product (20 mg) as a white solid. This was taken up in diethylether/dichloromethane (1:1) and a solution of oxalic acid (15 mg) in diethyl ether (1 ml) added. The resulting solid was filtered off and dried in vacuo to yield 4 mg of the title product as a hydroscopic white solid. MS APCI+ve m/z 278 [(M+H)+]. 1H NMR 400 MHz (d4-MeOH) 7.87 (1H, s), 7.66 (1H, d), 7.34 (1H, s), 7.22 (1H, d), 7.17 (1H, s), 3.21 (1H, m), 3.10 (1H, m), 2.73 (1H, ddd), 2.46 (1H, ddd).

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-Chloro-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Hamley, Peter; Mete, Antonio; Pimm, Austen; US2003/158185; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 33143-29-2, 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. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: PICP-n (4 mol%, based on Mn ion content in PICP-n), unfunction-alized alkenes (0.5 mmol) and pyridine N-oxide (0.095 g, 1 mmol)were added into dichloromethane (2 ml) under stirring. Buffered NaClO (1 mmol, pH = 11.5) as an oxidant was then added in four equal portions at 0C. The progress of epoxidation was moni-tored by GC. After the reaction, volatile solvents were evaporatedunder in a vacuum. PICP-n was precipitated out from reaction system by the addition of n-hexane (5 ml), washed withether (3 ¡Á 5 ml), dried in vacuum, and finally recharged withfresh solvents and reaction substrates for the next catalytic cycle.Supernatant was decanted and separated by separatory funnel.Aqueous phase was extracted with CH2Cl2for several times. Theextract was combined with organic phase. The collected organicphase was dried over anhydrous sodium sulfate and concen-trated in vacuum. Further purification of the residue by flashcolumn chromatography afforded pure epoxides. The conversionsand ee values were measured by a 6890 N gas chromatograph(Agilent Co.) equipped with a chiral capillary column (HP19091G-B213, 30 m ¡Á 0.32 mm ¡Á 0.25 m) and a FID detector. Nitrogenwas used as the carrier gas with a flow of 30 ml min-1. The injector temperature is 250C, and the detector temperatureis also 250C. The retention times of the corresponding chiralepoxides (tabsolute configuration) are as follows: (a) styrene epox-ide: the column temperature is 90C, tR= 15.2 min, tS= 15.7 min;(b) -methylstyrene epoxide: the column temperature is 80C,tS= 16.3 min, tR= 16.5 min; (c) indene epoxide: the column tem-perature was programmed from 80 to 180C with 8C min-1,tSR= 11.5 min, tRS= 11.9 min; (d) 1,2-dihydronaphthalene epox-ide: the column temperature was programmed from 80 to180C with 6C min-1, tSR= 13.4 min, tRS= 13.6 min; (e) 6-cyano-2,2-dimethylchromene epoxide: the column temperature wasprogrammed from 80 to 200C with 4C min-1, tSS= 24.0 min,tRR= 24.3 min; (f) 6-nitro-2,2-dimethylchromene epoxide: the col-umn temperature was programmed from 80 to 200C with 4C min-1and retained at 200C for 5 min, tSS= 30.3 min,tRR= 30.8 min.

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

Reference:
Article; Chen, Yaju; Tan, Rong; Zhang, Yaoyao; Zhao, Guangwu; Zheng, Weiguo; Luo, Rongchang; Yin, Donghong; Applied Catalysis A: General; vol. 491; 1; (2015); p. 106 – 115;,
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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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 501-00-8

To a mixture of 5.8 mL (50 mmol) of 3- fluorophenylacetonitrile (5), 8.3 mL (100 mmol) of 1- bromo-2-chloroethane, and 0.23 g (1.0 mmol) of benzyltriethylammonium chloride was added 28 mL of 50% aqueous sodium hydroxide solution, and the resulting mixture was stirred at 40C for 3 hours [M. FEDORYNSKI and A. JONCZYK Org. Prep. Proc. Intl. (1995) 27,355- 3591. At this point 25 mL of ethylene glycol was added, and the mixture then was stirred at 100C for another 20 hours. After cooling to room temperature, the reaction mixture was diluted with water and then washed with ethyl acetate. The aqueous phase was adjusted to pH 2 employing hydrochloric acid and then extracted with diethyl ether. The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to provide 8.1 g of 1- (3- fluorophenyl) cyclopropane-l-carboxylic acid (6). NMR (300 MHz, DMSO-D6) 12.41 (br s, 1 H), 7.37-7. 29 (m, 1 H), 7.18-7. 03 (m, 3 H), 1.45 (d of d, 2 H), 1.17 (d of d, 2 H).

According to the analysis of related databases, 501-00-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2004/43911; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 1503-49-7, The chemical industry reduces the impact on the environment during synthesis 1503-49-7, name is 4-Benzoylbenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: 2-Furonitrile 1m (186 mg, 2 mmol), NaN3 (260 mg, 4 mmol), BiCl3 (126 mg, 0.4 mmol), and 8 mL of a 3:1 isopropanol/water mixture were added to a 30-mL Pyrex microwave vessel, which was then capped. The microwave vessel was then placed in a Milestone Start Synth microwave reactor. The reaction was magnetically stirred and heated for 1 h at 150C. The reaction was monitored by thin-layer chromatography (TLC) using an ether/hexane mixture (typically 50/50) for development. The reaction mixture was then diluted with saturated aqueous sodium bicarbonate (20 mL) and was hed with ethyl acetate (2¡Á15 mL). The aqueous sodium bicarbonate layer was cooled with ice and acidified to a pH of 2 or less with concentrated hydrochloric acid, which was added dropwise. The precipitate formed was extracted with ethyl acetate (3¡Á15 mL). The combined organic layers were dried with anhydrous sodium sulfate and decanted into a tared round-bottom flask. The organic layer was concentrated under reduced pressure by rotary evaporation at 40C and then under high vacuum. The tetrazole product was recrystallized from ethyl acetate and hexane.

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

Reference:
Article; Coca, Adiel; Feinn, Liana; Dudley, Joshua; Synthetic Communications; vol. 45; 8; (2015); p. 1023 – 1030;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, 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 326-62-5, category: nitriles-buliding-blocks

Step 1: 4- (2 -Fluorophenyl) tetrahydropyran-4-carbonitrile To a solution of 2-(2-fluorophenyl)acetonitrile (10.0 g,74.07 rnmol) in DMSO (300 mL) was added sodium hydride (6.8 g,170.37 mmol) at 0C portion wise. After 30 minutes, 1-chloro- 2-(2-chloroethoxy)ethane (6.2 mL, 62.9 rnmol) was added theretoin dropwise manner, and the reaction mixture was heated at 75C under nitrogen for 3 hours. The product formation was confirmed by TLC, then the reaction mixture was poured into ice cold water (3000 mL) and extracted with ethyl acetate (3x 100 mL) . The combined organic layers were washed with brine,dried over sodium sulfate and concentrated under vacuo. The residue thus obtained was purified by column chromatography using 5-8% ethyl acetate in hexane as a mobile phase to give the title compound (8.5 g, 56%)MS(EI)m/z: 206.1 (M + 1); ?H NMR (400 MHz, CDC13): 2.16-2.19(m, 2H), 2.23-2.30 (m, 2H), 3.91-3.97 (m, 2H), 4.08 (dd, J =3.6 & 11.6 Hz, 2H), 7.11-7.17 (m, 1H), 7.16-7.22 (m, 1H),7.34-7.37 (m, 1H), 7.42-7.47 (m, 1H)

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; DESHPANDE, Anil M.; BARAWKAR, Dinesh; PATIL, Santosh; BANKAR, Digambar; (178 pag.)WO2016/88903; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

4110-35-4, name is 3,5-Dinitrobenzonitrile, 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. category: nitriles-buliding-blocks

General procedure: The procedure for the synthesis of the tetrazole 2a is representative. A mixture of sodium azide (0.39 g 0.0060 mol), urea (0.36 g, 0.0060 mol) and water (2.5 mL) was taken in a round-bottom flask and stirred at 60 C for 1 h. Charged benzonitrile 1a (0.5 g 0.0048 mol), acetic acid(0.5 mL) and DMF (2.5mL) at 60 C and heat to 110C stirred for 8 h. After completion of the reaction (as indicated by TLC), the reaction mixture was cooled to room temperature and diluted the reaction mass with water (2.5 mL)and ethyl acetate (5.0 mL) at 25-35 C. Add 5N aqueous hydrochloric acid (2.5 mL) at 25-35 C. Stirred for 20- 30 min, the resultant organic layer was separated and the aqueous layer was extracted with ethyl acetate (2.5 mL). The combined organic layer was washed with 40 % aq.NaCl solution (2.5 mL) and dried over anhydrous Na2SO4 and concentrated to give a crude product, which was isolated using chilled water after 3-4 h maintenance, and eventually filtered off to give 0.67 g (95%) of an off-white solid.

The synthetic route of 4110-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yakambram; Jaya Shree; Srinivasula Reddy; Satyanarayana; Naveen; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 59; 5; (2018); p. 445 – 449;,
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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. 17626-40-3, name is 3,4-Diaminobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H7N3

General procedure: Ethyl-2-oxo-2-(6-phenylimidazo[2,1-b]thiazol-5-yl)acetate (4a,0.3 g, 0.9 mole) and O-phenylenediamine (5a, 0.108 g, 0.9 mole) were mixed properly and was charged into a specially designed microwave test tube and acetonitrile (5 mL) was added to this mixture and was irradiated for 35 min at 200C and 250 psi pressure. After cooling, the solid mass was crushed into 50 ml cold acetonitrile. The solid mass was filtered and the filtrate was discarded. After washing several time with cold acetonitrile, the solid mass was dried under vacuum to get the 3-(6-Phenylimidazo[2,1-b]thiazol-5-yl)quinoxalin-2(1H)-ones (6a). The related compounds (6b-q) were prepared in the same way

According to the analysis of related databases, 17626-40-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mukherjee, Chandrani; Watanabe, Kenneth T.; Biehl, Edward R.; Tetrahedron Letters; vol. 53; 45; (2012); p. 6008 – 6014;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts