Author: Jessica.F

Application of 21524-39-0,Some common heterocyclic compound, 21524-39-0, name is 2,3-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

D) 3-fluoro-2-(3-iodo-4-methoxy-1H-pyrazolo[4,3-c]pyridin-1-yl)benzonitrile [1067] To a solution of 3-iodo-4-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (1.6 g) in dichloromethane (15 mL) was added trifluoroacetic acid (5 mL) at room temperature, and the mixture was stirred for 5 hr. To the reaction mixture was added aqueous sodium carbonate solution. The organic layer was separated, and concentrated under reduced pressure. A mixture of the obtained residue (0.80 g), 2,3-difluorobenzonitrile (0.50 g) and potassium carbonate (0.60 g) in DMF (3 mL) was stirred at 100C for 5 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (0.80 g). MS (ESI+): [M+H]+395.0. MS(ESI+), found: 395.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Difluorobenzonitrile, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NARA, Hiroshi; DAINI, Masaki; KAIEDA, Akira; KAMEI, Taku; IMAEDA, Toshihiro; KIKUCHI, Fumiaki; EP2857400; (2015); A1;,
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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. 34667-88-4, name is 2-Fluoro-4-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Fluoro-4-nitrobenzonitrile

A solution of 66 6 (10.0g, 60.24mmol) in 69 methanol (100mL) was hydrogenated with 10% 70 Pd/C (1.0g) under hydrogen atmosphere at room temperature for 12h. After filtration, the filtrate was evaporated to give the corresponding product. It was obtained as a gray 16 solid in 88% yield. 7 was ready for the next step without the further purification. HRMS (ESI): m/z, calculated for C7H5FN2 137.0487 (M+H)+, found 137.0452.

The synthetic route of 34667-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Xi; Ge, Raoling; Li, Lei; Wang, Jubo; Lu, Xiaoyu; Xue, Siqi; Chen, Xijing; Li, Zhiyu; Bian, Jinlei; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1325 – 1344;,
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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. 5332-06-9, name is 4-Bromobutanenitrile, A new synthetic method of this compound is introduced below., SDS of cas: 5332-06-9

(R)-3-(2-amino-2-phenylethyl)-1′-(3-chlorobenzyl)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-1H-spiro[furo[3,4-d]pyrimidine-5,4′-piperidine]-2,4(3H,7H)-dione (1-16) (10 g, 15 mmol) was dissolved in acetonitrile (200 mL), and then NaI (6.2 g, 45 mmol), K2CO3 (6.8 g, 45 mmol) and 4-bromobutanenitrile (2.3 mL, 22.5 mmol) were added to the mixture in sequence, followed by stirring for 12 hrs at 95 C. The resulting solution was cooled down to room temperature, filtered, and concentrated under reduced pressure to remove acetonitrile therefrom. The resulting solution was diluted with dichloromethane, washed with a saturated aqueous ammonium chloride solution, and the organic layer was separated. The organic layer was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography (eluent: dichloromethane/methanol=98/2?95/5) and dried under vacuum to obtain the title compound as white foam (8.2 g, yield: 75%).

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; SK CHEMICALS CO., LTD.; Kim, Seon-Mi; Kim, Jae-Sun; Lee, Minhee; Lee, So-young; Lee, Bong-Yong; Shin, Young Ah; Park, Euisun; Lee, Jung A; Han, Min-Young; Ahn, Jaeseung; Yoo, Taekyung; Kim, Hun-Taek; US2015/166558; (2015); 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. 215800-25-2, name is 2-(4-Bromo-3-methylphenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(4-Bromo-3-methylphenyl)acetonitrile

A mixture of 2-(4-bromo-3 -methylphenyl)acetonitrile (1 .50 g, 7.14 mmol, 1.0 eq), (2-fluorophenyl)boronicacid (1.19 g, 8.56 mmol, 1.2 eq), CsF (2.38 g, 15.70 mmol, 2.2 eq), Pd(PPh3)4 (0.41 g, 0.35 mmol, 0.05 eq) in DMF (15 mL) was stirred at 90 C under nitrogen atmosphere for 18 h. After complete consumption of starting material, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate. The organic extract was separated and the aqueousextract was again extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous Na2SO4, filtered and solvents evaporated from the filtrate under reduced pressure to obtain a crude, which was purified by flash chromatography on silica gel, 23 0-400 mesh, using gradient of ethyl acetate in hexanes as eluent to obtain 2-(2?-fluoro-2- methyl-[1,1?-biphenyl]-4-yl)acetonitrile as yellow oil, yield (1.12 g, 70%).

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 215800-25-2.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; BARTA, Thomas, E.; BOURNE, Jonathna, William; MONROE, Kyle, D.; MUEHLEMANN, Michael, M.; PANDEY, Anjali; BOWERS, Simeon; (59 pag.)WO2017/34990; (2017); 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. 14377-68-5, name is 1-Phenylcyclobutanecarbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C11H11N

Potassium nitrate (7.88 g, 77.0 mmol) was suspended in sulfuric acid (45 mL) at 0 C. and stirred for 30 minutes until a clear and colorless solution was obtained (NOTE-a blast shield is highly recommended). An addition funnel was charged with 1-phenylcyclobutanecarbonitrile (11.40 g, 72.5 mmol), and this neat starting material was added drop wise at such a rate that the internal reaction temperature did not exceed 10 C. Upon completion of the addition (which required 90 min), the mixture was poured onto 300 g of ice and stirred vigorously for 30 minutes. The resulting suspension was filtered, and the solid was washed with water and dried under vacuum to afford give 1-(4-nitrophenyl)cyclobutanecarbonitrile (13.53 g, 92%) as a light tan powder. 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 2.11-2.21 (m, 1H) 2.47-2.58 (m, 1H) 2.66 (s, 2H) 2.88-2.96 (m, 2H) 7.63 (d, J=8.54 Hz, 2H) 8.29 (d, J=8.54 Hz, 2H).

The synthetic route of 14377-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; pfizer Inc; US2010/197591; (2010); 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 6574-99-8 as follows. SDS of cas: 6574-99-8

The solvent and catalyst recovered in Example 2 were used for feeding.1) In the reaction kettle with a reflux water separation device, add the anhydrous aprotic polar solvent 1,3-dimethylimidazoline used in Example 2 and make up 2000 kg with a new solvent.Raw materials 3,4-dichlorobenzonitrile 1000 kg, water agent 200 kg toluene, heated to 90 ~ 120 reflux, water separation for 1 to 2 hours, until the water in the kettle <0.05% 2) Add 800 kg of potassium fluoride and 45 kg of catalyst to the reaction kettle, raise the temperature to 130 150 , and reflux for 2 to 3 hours; 3) Turn on the vacuum pump, the vacuum degree is -0.1MPa, the top temperature of the reaction kettle tower is 90-115 C, and the toluene is collected, and the fractions are collected; 4) Continue to increase the temperature. When the temperature in the reactor reaches 190 200 and the top temperature reaches 170-180 , the crude 3,4-difluorobenzonitrile will be collected. When the content of 3,4-difluorobenzonitrile in the reactor is at At 89.0-89.5%, the reaction is deemed complete and the crude product is 818 kg; 5) Turn off the hot oil pump, turn on the cold oil system, the temperature in the reaction kettle drops below 100 C, put the materials in the reaction kettle into a centrifuge, the filtrate is pumped into the reaction kettle for the next feeding, and the solid materials are bagged; 6) The crude product 3,4-difluorobenzonitrile is drawn into the rectification kettle, stirring is started, and the fractions of 179-181 C are collected at elevated temperature and pressure to obtain the finished product 3,4-difluorobenzonitrile 743 kg, content 99.63%, yield 93.0%; after distillation, the residual liquid is sent to the reactor for the next feeding. According to the analysis of related databases, 6574-99-8, the application of this compound in the production field has become more and more popular. Reference:
Patent; Ji’ning Kangsheng Rainbow Biological Technology Co., Ltd.; Qian Jidong; Huang Dingqian; Sheng Rui; Yan Weiwei; (8 pag.)CN110804001; (2020); A;,
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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. 110301-23-0, name is 4-Amino-3,5-difluorobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H4F2N2

The benzaldehyde used as starting material was prepared as follows; To a stirred solution of 4-amino-3,5-difluorobenzonitrile (2.Og, 12.98mmol) in toluene (16ml) was added dropwise DIBAL (1.5M in toluene) at O0C. The reaction mixture was warmed to RT and stirring continued for 2h. The reaction was quenched by dropwise addition to 10% aq citric acid (10ml). EtOAc (50ml) and saturated aq potassium sodium tartrate (Rochelle’s salt) (30ml) were added and the mixture was vigorously stirred for 20min. The organic layer was isolated and washed with water (10ml), dried (Na2SO4), filtered and concentrated to dryness to give a pale yellow solid (1.9g, 93%). LCMS purity 92%, m/z 158 [M+H]+.

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; CHROMA THERAPEUTICS LTD.; WO2007/129040; (2007); A1;,
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Synthetic Route of 67832-11-5, 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 67832-11-5 as follows.

4-Bromo-2-bromomethylbenzonitrile (TJA01043) C8H5Br2N MW 274.94. 4-Bromo-2-methylbenzonitrile (5.00 g, 25.5 mmol), N-bromosuccinimide (4.99 g, 28.1 mmol), benzyl peroxide (0.198 g, 0.816 mmol) and carbon tetrachloride (100 mL) were loaded to a r.b. flask and set to reflux (79 C) for 6 h. Once cooled the succinimide was filtered off and carbon tetrachloride removed via a dry ice-acetone cooled rotary evaporator. The residues were dissolved in dichloromethane (100 mL) and washed with distilled H2O (50 mL x 3) and brine (50 mL x 2). Dried over Na2SO4 and solvent removed in vacuo to leave yellow residues. Column chromatography (hexane/dichloromethane 60:40) eluted the title compound as a yellow solid. Recrystallisation (cyclohexane) gave a white crystalline solid (5.07 g, 73 %), mp 61.7-77.2 0C; i?/ 0.30 (hexane/dichloromethane 60:40), c.f. 0.36 (dibromobenzylbromide), 0.36 (4- bromo-2-methylbenzonitrile) ;HPLC (60 % CH3CN in H2O) R, 3.130 (50.62 %), 2.701 (42.38 %, dibromobenzylbromide) ; MS (EI), m/z 274.0 (M- – H, 34 %).

According to the analysis of related databases, 67832-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STERIX LIMITED; WO2007/68905; (2007); A1;,
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Related Products of 243128-37-2, A common heterocyclic compound, 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile, molecular formula is C8H6FNO, 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.

A suspension of NaH (1.25 eq) in DMF (100 ml), to which is added 10 g of the product obtained during the preceding step, is stirred for 1 h at AT, then 4-fluoro-3-methoxy-benzonitrile (1 eq) in DMF (100 ml) is added and stirred a further 24 h at AT. After evaporation to dryness, the residue is redissolved in water, extracted with TBME, the organic layer is washed with a 1 N aqueous solution of NaOH then with an aqueous NaCl solution, dried over MgSO4, filtered and evaporated. 10.1 g of the desired product are isolated after chromatography on silica eluting with a DCM/MeOH/NH4OH mixture (97.5:2.5:0.1 v/v/v).

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; CEREP; US2009/233910; (2009); A1;,
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50712-68-0, name is 4-Chloro-2-methylbenzonitrile, 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. name: 4-Chloro-2-methylbenzonitrile

General procedure: A solution of 1-acetyl-4-acetoxy-4-phenylazo-1,2,3,4-tetrahydroquinoline (8,0.25 mmol) in dry CH2Cl2 (2 mL) was added dropwise slowly to a mixture ofnitrile 9 (0.35 mmol) and AlCl3 (0.35 mmol) in CH2Cl2 (5 mL) at -40 C under an atmosphere of nitrogen (exothermic). After stirring at this temperature for0.5 h, the reaction was allowed to warm to room temperature and stirred foradditional 1 h. Then the mixture was cooled to 0 C and extracted with H2O(1 mL 3). The combined aqueous phase was concentrated under reducedpressure and purified by reverse flash column chromatography. The collectedfractions were lyophilized to afford the respective5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepinium salt 10.For the chloride salt 10, reverse flash column chromatography conditions wereas follows: C18, acetonitrile = 5% in H2O and acetonitrile; 0.5% hydrochloricacid in H2O. For the trifluoroacetic salt 10, the reverse flash columnchromatography conditions were: C18, acetonitrile = 5% in H2O andacetonitrile; 0.5% trifluoroacetic acid in H2O.The picric salts 10 were obtained by exchanging the Cl- or CF3COO- anion bytreatment with picric acid. The following procedure was representative: 0.9-1.1%picric acid solution was added dropwise into the corresponding salt 10dissolved in H2O (1 mL) and a brown suspension appeared. The picric acidsolution was added dropwise continually until no further suspension appeared.The mixture was filtered, and the filtered cake was washed with H2O (0.5 mL 2), collected and dried in vacuum to give the picric salt 10.

The synthetic route of 50712-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Luan, Lin-bo; Song, Zi-jie; Li, Zhi-ming; Wang, Quan-rui; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1826 – 1833;,
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