Month: May 2021

These common heterocyclic compound, 64113-85-5, name is 4-Methyl-[1,1′-biphenyl]-2-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. Formula: C14H11N

General procedure: The heterocyclic derivative (0.99 mmol) and 5 mL THF is cooled to -78 oC, n-BuLi solution ( 0.5, mL, 1.2 eq) is added, the mixture is stirred 1 hr, after which 2-cyano-4-methyhlbiphenyl (192 mg, 0.99 mmol, dissolved in 5 mL THF) is added dropwise, The solution is then stirred 1 hr at -78 oC, then allowed to warm to room temperature and stirred for 6 hr. After this, 10 mL of 6M HCl is added and the mixture is stirred overnight. The solution is then basified with 10M NaOH and the products are partitioned between ether and water. The aqueous layer is further extracted (2x with ether) and the combined extracts are washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent is then removed under reduced pressure and the crude mixture is purified by column chromatography (1:1, hexanes: ethyl acetate).

The synthetic route of 4-Methyl-[1,1′-biphenyl]-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stentzel, Michael R.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 60; 25; (2019); p. 1675 – 1677;,
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Adding a certain compound to certain chemical reactions, such as: 91132-15-9, name is 2-(4-(Hydroxymethyl)phenyl)-2-methylpropanenitrile, 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 91132-15-9, Safety of 2-(4-(Hydroxymethyl)phenyl)-2-methylpropanenitrile

a- Synthesis of Int. 51 : To a suspension of 7 (2.5 g, 1 1 .3 mmol ), 2-[4-(hydroxymethyl)phenyl]-2- methylpropanenitrile (1.8 g, 10.3 mmol ), PPh3 supp (3.8 g, 12.3 mmol ) in d y DCM (50 mL) was added DBAD (2.8 g, 12.3 mmol) and the r.m. was stirred at r.t. for 18 h. The mixture was filtered through Celite, washed with DCM and the filtrate was evaporated until dryness. The residue (7g) was purified by prep. LC (irregular SiOH 35-40muiotaeta, 90g GraceResolv, gradient from 95% heptanes, 5% EtOAc to 80% heptanes, 20%> EtOAc). The fractions were collected and evaporated until dryness to give 2. lg of Int. 51 (54%).

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-(4-(Hydroxymethyl)phenyl)-2-methylpropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEVELLEC, Laurence, Anne; PASQUIER, Elisabeth, Therese, Jeanne; DESCAMPS, Sophie; MERCEY, Guillaume, Jean, Maurice; WROBLOWSKI, Berthold; VIALARD, Jorge, Eduardo; MEERPOEL, Lieven; JEANTY, Matthieu, Ludovic; JOUSSEAUME, Thierry, Francois, Alain, Jean; WO2015/144799; (2015); A1;,
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Reference of 1211596-75-6, 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 1211596-75-6 as follows.

Step 4: 2-(Hydroxymethyl)-6-(trifluoromethyl)benzonitrile To a solution of LiBH4 (3.3 g, 153 mmol) in THF (100 mL) was added methyl 2-cyano-3- (trifluoromethyl)benzoate (14 g, 61 mmol). The mixture was stirred at room temperature for 2 h. The mixture was concentrated in vacuo to give the crude product, which was diluted with water, and extracted with EtOAc. The organic layer was separated, dried over Na2S04, filtered, and concentrated to give the crude product 2-(hydroxymethyl)-6- (trifluoromethyl)benzonitrile (10 g, 77% yield): 1H NMR (400 MHz, CDC13) delta 7.83-7.72 (m, 3H), 5.46 (s, 2H); ES-LCMS m/z 202.1 (M+H).

According to the analysis of related databases, 1211596-75-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; KEENAN, Richard, M.; MILLER, Aaron, Bayne; QIN, Donghui; WO2013/177349; (2013); A2;,
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Adding a certain compound to certain chemical reactions, such as: 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile, 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 4421-09-4, Computed Properties of C8H5NO2

5-(1,3-benzodioxol-5-yl)-1H-tetrazole was synthesized from 1,3-benzodioxole-5-carbonitrile by following a reported procedure [46]. The requisite nitrile (2) was prepared from Piperonal (1,3-benzodioxole-5-carbaldehyde) via oxime formation, followed by dehydration with acetic anhydride, following a reported procedure [45]. Nitrile (2.95 g, 20 mmol), sodium azide (1.43 g, 22 mmol) and zinc bromide (4.50 g, 20 mmol), were put in 60 mL of water. 5 mL of isopropanol was also added to stop the formation of clumps. The reaction mixture was refluxed for 24 h and monitored by TLC; vigorous stirring is essential. After 24 h HCl (3 N, 30 mL) and ethyl acetate (100 mL) were added, and vigorous stirring was continued until no solid was present and the aqueous layer had a pH of 1. If necessary, additional ethyl acetate was added. The organic layer was isolated and the aqueous layer extracted with 2 × 100 mL of ethyl acetate. The combined organic layers were evaporated, 200 mL of 0.25 N NaOH was added, and the mixture was stirred for 30 min, until the original precipitate was dissolved and a suspension of zinc hydroxide was formed. The suspension was filtered, and the solid washed with 20 mL of 1 N NaOH. To the filtrate was added 50 mL of 3 N HCl with vigorous stirring causing the tetrazole to precipitate. The tetrazole was filtered and washed with 2 × 50 mL of 3 N HCl and dried in a drying oven to furnish the tetrazole as a white powder.

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:
Article; Wani, Mohmmad Younus; Bhat, Abdul Roouf; Azam, Amir; Choi, Inho; Athar, Fareeda; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 313 – 320;,
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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. 53312-78-0, name is 3-Amino-5-chlorobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Amino-5-chlorobenzonitrile

A mixture of 3-amino-5-chloro-benzonitrile (2.4 g, 15.7 mmol), 4-chloro-2-methyl- benzaldehyde (2.4 g, 15.7 mmol) and 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (2.9 g, 15.7 mmol) in acetic acid (15 mL) was stirred at 120C for 16 h. The reaction mixture was allowed to cool to rt, concentrated, diluted with acetonitrile (15 mL), and stirred for 4 h at rt The resulting precipitate was collected by vacuum filtration and dried to afford 1.8 g of the title compound. tR: 6.50 min (HPLC 2); ESI-MS: 429 [M+H]+(LC-MS 2); Rf= 0.27(hexane/EtOAc, 1 :1 ).

The synthetic route of 53312-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; MAH, Robert; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/80141; (2013); A1;,
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Related Products of 157662-77-6, These common heterocyclic compound, 157662-77-6, name is 4-Fluoro-3-nitrophenylacetonitrile, 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 mixture of 2-(4-fluoro-3-nitrophenyl)acetonitrile (5.8 g, 32.2 mmol) and diisobutyl amine (20.8 g, 161 mmol) was stirred at 130C under N2 atmosphere for 2 hr. The resulting mixture was partitioned between EtOAc and H20. The layers were separated and the organic layer was washed with brine, dried over Na2S04, filtered and concentrated to give the crude product which was purified by flash chromatography (silica gel, 0-20% EtOAc in PE) to afford the title compound (8.0 g, 86% yield). LCMS (ESI) m/z calcd for Ci6H23N302: 289.18. Found: 290.76 (M+1 )+.

The synthetic route of 157662-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DE LA ROSA, Martha Alicia; KAZMIERSKI, Wieslaw Mieczyslaw; SAMANO, Vicente; (369 pag.)WO2018/116107; (2018); A1;,
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Synthetic Route of 877131-92-5, 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 877131-92-5 as follows.

Add hydrochloric acid (2 mL, 12M) to a solution of 2-[ 4-bromo-2(trifluoromethyl)phenyl]acetonitrile (600 mg, 2.25 mmol) in acetic acid (2 mL), the mixture is stirred at 100 C for 2 h under nitrogen. The reaction mixture is concentrated to afford title 5 compound (600 mg, 89.5%) as colorless oil. 1H NMR (400MHz, CD3Cl) () = 7.82 (d, J = 1.6 Hz, 1H), 7.67 (dd, J = 1.6, 8.4 Hz, 1H), 7.29 (s, 1H), 3.83 (s, 2H).

According to the analysis of related databases, 877131-92-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; MA, Tianwei; WU, Liang; ZHANG, Xuejun; (109 pag.)WO2019/41340; (2019); A1;,
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Reference of 80517-21-1,Some common heterocyclic compound, 80517-21-1, name is 4-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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.

Example 106(1)2-Amino-4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamide (106a)Compound (6b) (0.335 g) was dissolved in DMF (8.6 mL), and sodium hydride (0.097 g, a 55% dispersion in paraffin liquid) was added to the resulting solution at 0 C., followed by stirring for 30 min. Then, 4-fluoro-2-nitrobenzonitrile was added to the reaction solution, followed by stirring at 60 C. for 30 min. Water was added to the reaction solution, and the precipitate was collected by filtration and washed by sprinkling water to obtain 4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile (0.5 g, 85%). 4-{4-Chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile (0.35 g) and ammonium chloride (0.35 g) were dissolved in a solvent mixture of THF (3 mL), methanol (3 mL), and water (3 mL). Iron (0.57 g) was added to the resulting solution, followed by stirring at 70 C. for 1 hr. Insoluble matters were filtered by celite, and the solvent was distilled away. The precipitate was washed with water and was collected by filtration to obtain compound (106a) (0.32 g, 95%) as a white solid.1H-NMR (DMSO-d6) delta: 8.57 (1H, d, J=4.88 Hz), 7.70 (1H, d, J=9.27 Hz), 7.60 (1H, d, J=1.95 Hz), 7.47 (1H, d, J=4.88 Hz), 7.45 (1H, dd, J=9.27, 1.95 Hz), 6.92 (2H, brs), 3.73 (1H, tt, J=6.83, 6.83 Hz), 1.43 (6H, d, J=6.83 Hz); LRMS (ESI) m/z 330 [M+H]+.

The synthetic route of 80517-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; US2012/108589; (2012); A1;,
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Electric Literature of 395675-23-7,Some common heterocyclic compound, 395675-23-7, name is 2-Chloro-5-fluorophenylacetonitrile, molecular formula is C8H5ClFN, 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.

[0591] To a solution of (2-chloro-5-fluorophenyl)acetonitrile (10.0 g, 59.0 mmol) in THF (75 ml) under argon was added gradually while stirring, at -78C., a 2 M solution of LDA in THF (44 ml, 88 mmol). The mixture was allowed to come to 0C. and, after 15 min, cooled back down again to -78C. Subsequently, tert-butyl 3-bromopropanoate (11 ml, 71 mmol) was slowly added dropwise thereto at -78C. while stirring. Stirring of the mixture was continued overnight, in the course of which the cooling bath (dry ice/acetone) was allowed to come gradually to RT. Subsequently, water was added gradually to the mixture, which was extracted twice with ethyl acetate. The combined organic phases were washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated, and the residue was purified by flash column chromatography (340 g silica gel Biotage Snap-Cartridge KP-Sil, cyclohexane/ethyl acetate gradient 93:7?3:7, Isolera One). The combined target fractions were concentrated and the residue was dried under reduced pressure. This gave 14.8 g (93% purity, 78% of theory) of the title compound. [0592] LC-MS (Method 1): Rt=2.22 min; MS (ESIpos): m/z=298 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5-fluorophenylacetonitrile, its application will become more common.

Reference:
Patent; Bayer Aktiengesellschaft; Bayer Pharma Aktiengeseiisehaft; BECK, Hartmut; KAST, Raimund; MEININGHAUS, Mark; DIETZ, Lisa; FUERSTNER, Chantal; STELLFELD, Timo; ANLAUF, Sonja; VON BUEHLER, Clemens-Jeremias; BAIRLEIN, Michaela; ANLAHR, Johanna; MUENSTER, Uwe; TERJUNG, Carsten; JOERISSEN, Hannah; HAUFF, Peter; MUELLER, Joerg; DROEBNER, Karoline; NAGEL, Jens; (220 pag.)US2020/31775; (2020); A1;,
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Electric Literature of 447-60-9, These common heterocyclic compound, 447-60-9, name is 2-(Trifluoromethyl)benzonitrile, 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.

General procedure: The mixture of 1-ferrocenyl-2-methylpropan-1-ol (1) (645 mg, 2.5 mmol) and the nitrile 2 (2.5 or 3.0 mmol) in DCE(5 mL) was added dropwise with vigorous stirring to MsOH (1.30 mL, 20 mmol) at room temperature. The resulting mixture was then heated with stirring at 60 C for the noted reaction time. After, the reaction mixture was cooled to roomtemperature, poured into a mixture of crushed ice (20 g) and 25% aq NH3 (6 mL) and extracted with EtOAc (80 mL × 3). The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the crude mixture by silica gel column chromatography gave the desired product 3

Statistics shows that 2-(Trifluoromethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 447-60-9.

Reference:
Article; Rozhkova, Yuliya S.; Plekhanova, Irina V.; Gorbunov, Alexey A.; Stryapunina, Olga G.; Chulakov, Evgeny N.; Krasnov, Victor P.; Ezhikova, Marina A.; Kodess, Mikhail I.; Slepukhin, Pavel A.; Shklyaev, Yurii V.; Tetrahedron Letters; vol. 60; 11; (2019); p. 768 – 772;,
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