Category: nitriles-buliding-blocks

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. 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5-methoxybenzonitrile

2-Bromo-5-methoxybenzonitrile (1.32 g, 6.23 mmol), 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (1.36 g, 6.23 mmol), bis(triphenylphosphine)palladiumdichloride (0.437 g, 0.623 mmol) and potassium phosphate monohydrate (4.30 g, 18.68 mmol) were added to toluene (30 mL) and water (3 mL). The reaction mixture was degassed with bubbled nitrogen gas for 30 minutes before being refluxed under nitrogen for 15 h. After cooling, the reaction mixture was filtered through Celite and the organic layer was extracted with ethyl acetate. After removal of the solvents, the crude material was triturated with 40 mL of DCM followed by 50 mL of hexanes to give 8- methoxyphenanthridin-6-amine (0.95g, 68%) as a light yellow solid. The product was confirmed by GC/MS and NMR.

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; UNIVERSAL DISPLAY CORPORATION; XIA, Chuanjin; YEAGER, Walter; LI, David Zenan; FIORDELISIO, James; MA, Bin; ELSHENAWY, Zeinab; LAYEK, Suman; BARRON, Edward; KOTTAS, Gregg; BROOKS, Jason; WO2012/116231; (2012); A2;,
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Application of 77532-78-6, The chemical industry reduces the impact on the environment during synthesis 77532-78-6, name is 2-Bromo-6-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

A. N-Butyl-2,3-difluoro-N-[1-(2-piperidin-1-ylmethyl-benzyl)-1H-benzoimidazol-2-ylmethyl]-benzamide A solution of 35 g (0.18 mole) of cyanobromotoluene and 16.18 g (0.19 mole) of piperidine in 300 mL of anhydrous DMF was treated with 73 g (0.5 mole) of K2CO3 at 50 C. for 2 hr. The reaction mixture was filtered through a plug of Celite, washed with 400 mL of ethyl acetate, and the filtrate was partitioned between ethyl acetate and 1/2 saturated brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, yielding 36 g (0.18 mole) 100% of 2-Piperidin-1-ylmethyl-benzonitrile. 1H NMR (300 MHz, CDCl3) 7.6 (m, 3H), 7.24 (m, 1H), 3.6 (s, 2H), 2.4 (m, 4H), 1.5 (m, 6H).

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-6-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DeSimone, Robert W.; Peterson, John; Steenstra, Cheryl; Shen, Yiping; Gustavson, Linda; Bakthavatchalam, Rajagopal; Hutchison, Alan; US2003/216390; (2003); A1;,
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Electric Literature of 13519-90-9, A common heterocyclic compound, 13519-90-9, name is 4-Fluoroisophthalonitrile, molecular formula is C8H3FN2, 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.

To (1R,3S)-cyclohexane-1,3-diamine (1.0 g, 8.8 mmol) and 4-fluoroisophthalonitrile (2.7 g, 18.4 mmol)Triethylamine (5.4 ml) was added to a solution of 30 ml of dimethyl sulfoxide. The mixture was purged with nitrogen and heated to stir at 150 C for 3 hours. After cooling to room temperature, the reaction mixture was diluted with water (100 ml) and extracted three times with dichloromethane (100 ml). The organic extracts were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography(230-600 mesh silica gel) purified,Elute with 0-80% ethyl acetate / hexane,Get the title compound,It was a white solid (2.6 g, 81% 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; Sichuan Yi Lite Bio-pharmaceutical Co., Ltd.; Jiao Guansheng; Zhang Chengpan; (13 pag.)CN109160888; (2019); A;,
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Synthetic Route of 38791-62-7, The chemical industry reduces the impact on the environment during synthesis 38791-62-7, name is 4-Phenoxyphthalonitrile, I believe this compound will play a more active role in future production and life.

11.3 g of compound 1 was dissolved in 30 ml of methanol, added to 25 ml of 50% sodium hydroxide solution, heated to reflux for 48 h. After completion of the reaction, the pH was adjusted to about 3 with concentrated hydrochloric acid, precipitated by precipitation, filtered and dried to give 10.5 g of compound 2.

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

Reference:
Patent; BEIJING BETA PHARMA, INC.; (43 pag.)TWI582078; (2017); B;,
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Reference of 867367-02-0, 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. 867367-02-0, name is 4-Fluoro-3,5-dimethylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 2-[4-Chloro-3-(4-cyano-2,6-dimethyl-phenoxy)-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide (I-55) step 1-A solution of 40 (0.600 g, 2.79 mmol), 3,5-dimethyl4-fluorobenzonitrile (41, 0.459 g, 3.07 mmol), K2CO3 (1.157 g, 8.37 mmol) and NMP (6 mL) was stirred and heated to 120 C. for 6 h. When the starting material was consumed the solution was cooled and acidified with 10% HCl and twice extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by SiO2 chromatography and eluted with an EtOAc/hexane gradient (100% hexane to 50% hexane) to afford 106a. Steps 2-4 were carried out as described in steps 7-9 of Example 1 which afforded I-55. Compound I-56 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 4-amino-2-methyl-benzenesulfonamide. Compound I-68 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 2-chloroaniline. Compound I-135 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 4-amino-2-chloro-benzenesulfonamide.

The synthetic route of 4-Fluoro-3,5-dimethylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2005/239880; (2005); A1;,
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Reference of 191014-55-8, A common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-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.

To a solution of the corresponding aryl fluoride (0.2 mmol) and the corresponding alcohol (0.200 mmol) in DMF (1 mL) is added 0.5 mL of 0.6 M slurry of sodium hydride (60%) in DMF (0.3 mmol). The resultant mixtures were shaken at room temperature for 48 hours. The reactions were quenched with water (0.5 mL). The solvent is evaporated in vacuo. To the concentrated reaction mixtures is added methylene chloride (3 mL) and water (2 mL). The organic layer is filtered through silica (0.5 g) solid phase extraction column and evaporated to yield material that was purified by reverse phase HPLC.

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; Pfizer Inc; US2009/170886; (2009); A1;,
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Reference of 874285-03-7,Some common heterocyclic compound, 874285-03-7, name is 3-Bromo-2-fluorophenylacetonitrile, molecular formula is C8H5BrFN, 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.

2-(3-bromo-2-fluorophenyl)acetonitrile (800 mg, 3.7 mmol,1 eq.) and (S)-1- iodo-2-(2-iodoethoxy)propane (1.27 g, 3.74 mmol, 1 eq.) were dissolved in dimethyl sulfoxide (10 ml_). Sodium hydride (331 mg, 8.3 mmol, 2.2 eq.) was added to the reaction mixture and stirred for 1 h at room temperature. The reaction mixture was diluted with water (10 ml_) and ethyl acetate (10 ml_), and the layers were separated. The organic phase was washed with 1 M HCI (1×10 ml_), water (1×10 ml_) and brine (1×10 ml_). The organic phase was concentrated under vacuum to afford a diastereomehc mixture of (2S,4R)-4- (3-bromo-2-fluorophenyl)-2-methyl-tetrahydro-2H-pyran-4-carbonitrile and (2S,4S)-4-(3-bromo-2-fluorophenyl)-2-methyl-tetrahydro-2/-/-pyran-4- carbonitrile (1 :1 ). The diastereomehc mixture was separated by reverse phase chromatography (40 – 90% acetonithle-water) to obtain the title compound (252 mg, 23%) as a single isomer. Stereochemistry confirmed by NMR. [2SAR)- 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 1.26 (d, J=6.2 Hz, 3 H) 1.81 (dd, J=13.2, 11.0 Hz, 1 H) 2.08 – 2.26 (m, 3 H) 3.89 – 4.02 (m, 2H) 4.04 – 4.16 (m, 1 H) 6.99 – 7.13 (m, 1 H) 7.32-7.44 (m, 1 H) (s, 1 H) 7.51 – 7.63 (m, 1 H); LC/MS (M+H) = 298 (100%), 300 (98.5%). (2S,4S): 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 1.22 (d, J=6.2 Hz, 3 H) 2.05 (dd, J=14.5, 10.7 Hz, 1 H) 2.25-2.44 (m, 1 H) 2.49 – 2.63 (m, 2 H) 3.44 – 3.59 (m, 2H) 3.86 – 3.99 (m, 1 H) 7.02 – 7.13 (m, 1 H) 7.19-7.31 (m, 1 H) (s, 1 H) 7.53-7.64 (m, 1 H); LC/MS (M+H) = 298 (100%), 300 (98.5%).

The synthetic route of 874285-03-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); 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. 3100-67-2, name is 1-Amino-2-naphthonitrile, A new synthetic method of this compound is introduced below., Safety of 1-Amino-2-naphthonitrile

A solution of [Intermediate 7-a] (18.5 g, 0.11 mol) in dimethyl formamide (200 mL) was stirred at 0 C. Drops of a solution of N-bromosuccinimide (20.1 g, 0.11 mol) in dimethyl formamide (100 mL) were slowly added over 1 hr. The reaction mixture was warmed to room temperature and stirred for 12 hrs. Following filtration with an excess of distilled water, the filtrate was washed with methanol and recrystallized in toluene and methanol to afford [Intermediate 7-b] (18.7 g): yield 69%.

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; SFC CO., LTD.; LEE, Chang-Hee; SEO, Hyun-JONG; YOON, Seo-Yeon; SHIM, So Young; KIM, Si-In; (214 pag.)US2018/233669; (2018); A1;,
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Some common heterocyclic compound, 53005-44-0, name is 2-Methoxy-6-methylbenzonitrile, molecular formula is C9H9NO, 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: 53005-44-0

To intermediate 145 (5.0 g, 34.03 mmol) in THF (50 ml), benzylmagnesium chloride (34 ml, 2M in THF, 68.02 mmol) was added at 0C over 30 min. and heated to reflux for 15 h. The reaction mixture was cooled to room temperature, 2N HC1 (200 ml) was added and again refluxed for 4h. The reaction mixture was cooled and extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate : petroleum ether to afford to afford the title compound as brown liquid (3.7 g , 45%). -NMR (delta ppm, CDCI3, 400 MHz): 7.30-7. 18 (m, 6H), 6.76 (m, 2H), 4.07 (s, 2H), 3.83 (s, 3H), 2.02 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 53005-44-0, its application will become more common.

Reference:
Patent; RHIZEN PHARMACEUTICALS SA; NAGARATHNAM, Dhanapalan; VAKKALANKA, Swaroop Kumar, V.S.; MUTHUPPALANIAPPAN, Meyyappan; VISWANADHA, Srikant; BABU, Govindarajulu; BHAVAR, Prashant, Kashinath; WO2012/151525; (2012); A1;,
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Synthetic Route of 31603-77-7,Some common heterocyclic compound, 31603-77-7, name is 4-Biphenylacetonitrile, molecular formula is C14H11N, 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.

General procedure: To a solution of arylacetonitrile (10 mmol) (2-(4-bromophenyl)acetonitrile) in dried THF (10 mL), LDA (2.0 M in THF, 20 mL, 40 mmol) was added under N2 atmosphere in an ice-bath. The solution was stirred at 45 C for 1 h. After cooling the reaction mixture again to 0 C, iodomethane (60 mmol) was added drop wise. The reaction was stirred overnight at room temperature, quenched by 4 N HCl at 0 C and then diluted with Et2O. The phases were separated and the aqueous phase was extracted with Et2O (3 times). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4. After filtration and concentration, the crude acid was purified by flash column chromatography to give the desired product as a white or pale yellow solid. The next step of the hydrolysis was done by the reported procedures.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Biphenylacetonitrile, its application will become more common.

Reference:
Article; Hajipour, Abdol R.; Khorsandi, Zahra; Tetrahedron Letters; vol. 61; 3; (2020);,
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