Month: April 2021

52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, 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. Recommanded Product: Ethyl 2-cyano-4,4-diethoxybutyrate

A solution of 55 in 50% TFA/DCM (10 niL) was stirred at room temperature for 17 h. The solution was concentrated to afford the title compound, which was used in the next step without purification.57 2-(4-(Morpholinomethyl)phenylamino)-7H-pyrrolo[2,3-rf]pyrimidin-4-ol (57)[0292] To a microwave reaction tube was charged with 56 (10.0 mmol), 2-cyano-4,4- diethoxy-butyric acid ethyl ester (2.3 g, 10.0 mmol) and NaOMe (25% by wt in MeOH; 15 mL) in EtOH (5 mL). The reaction tube was sealed and the solution irradiated with microwave at 160 0C for 30 min. After cooling to room temperature, the mixture was concentrated. The residue was taken up in water (10 mL) and the pH adjusted to 1 with 6M of HCl. The resulting solution was stirred at room temperature for 25 min and then the pH adjusted to 9 with concentrated 10% NaOH. The resulting solid was filtered, washed with water and dried under high vacuum to afford the title compound as a brown solid. The material was used in the next step without purification.

The synthetic route of 52133-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
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Synthetic Route of 621-50-1, The chemical industry reduces the impact on the environment during synthesis 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, I believe this compound will play a more active role in future production and life.

To an ice-cold slurry of 50% sodium hydride (2.17g, 90.4mmol) in anhydrous THF (15ml), was slowly added a solution of (3-nitro-phenyl)-acetonitrile (2.2g, 13.58mmol) in anhydrous THF (5ml). After 30 min, methyl iodide (6.67ml, 107mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred overnight. It was then quenched with ice- water. The compound was then extracted with ethyl acetate, the organic layer separated and washed with water, dried over anhydrous sodium sulphate, filtered and concentrated to oil. Column chromatography over silica gel by eluting with ethyl acetate/pet ether (5:95) gave 2-methyl-2-(3-nitrophenyl)- propionitrile (1. Ig, 43%) as a solid.

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-(3-Nitrophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F2G LTD; WO2006/123145; (2006); A1;,
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Electric Literature of 796600-15-2, 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. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Heat a slurry of 2-chloro-4-fluoro-3-methyl-benzonitrile (0.4 g, 2.36 mmol) and L-proline (2.11 g, 18.8 mmol) in N-methylmorpholine (1.6 mL) at 200 0C in a microwave for 30 min. Partition the reaction between 2N aqueous hydrochloric acid and ethyl acetate. Separate and extract the organic portion with 2N aqueous sodium hydroxide. Acidify the aqueous extract to pH 1 by adding concentrated EPO hydrochloric acid and back extract into ethyl acetate. Extract the combined organic portions with brine, dry over magnesium sulphate, filter, and concentrate under reduced pressure to give the title compound. (0.395 g, 63%) mass spectrum (m/e): 263(M-I); 1H NMR (300 MHz, CDCl3): delta 8.66(bs,lH0, 7.31(d, IH), 6.75(d, IH), 4.38(t,lH), 3.67(m, IH), 3.10(m,lH), 2.43(m,lH), 2.29(s,3H), 2.20-1.90(m.3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluoro-3-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/124447; (2006); A2;,
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Related Products of 1897-52-5, 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. 1897-52-5, name is 2,6-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Preparation of 2,6-difluorobenzenecarboximidamide: To a solution of 2,6-difluorobenzonitrile (20 g) in diethyl ether (200 mL) was added lithium bis(trimethylsilyl)amide (240 mL, 1M in THF) at 0 C. The reaction mixture was stirred overnight at room temperature. After that, methyl tert-butyl ether (150 mL) was added and the reaction was stirred for 10 min. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The aqueous layer was basified (pH: 12-14) and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound (16 g) as a white solid. ‘H-NMR (400.0 MHz, de-DMSO): delta = 7.46-7.38 (m, 1H), 7.13-7.08 (m, 2H), 6.51 (s large, 3H).

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

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; SCHWARZ, Hans-Georg; DECOR, Anne; GREUL, Joerg; TRAUTWEIN, Axel; HEILMANN, Eike Kevin; FISCHER, Reiner; LOeSEL, Peter; MALSAM, Olga; PORTZ, Daniela; ILG, Kerstin; SOMMER, Herbert; EILMUS, Sascha; SCHARWEY, Melanie; LISHCHYNSKYI, Anton; GEIBEL, Sven; GOeRGENS, Ulrich; HERBERT, Simon; TURBERG, Andreas; (124 pag.)WO2017/5717; (2017); A1;,
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These common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(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. COA of Formula: C8H3ClF3N

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

The synthetic route of 2-Chloro-4-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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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. 72054-56-9, name is 4-(2-Bromoethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-(2-Bromoethyl)benzonitrile

Production Example 12 Synthesis of 4-carbamoylphenethyl bromide 4-Cyanophenethyl bromide (0.997 g) was dissolved in sulfuric acid (20 ml) and stirred at room temperature for 15 hr. Then it was poured into ice, diethyl ether was added thereto and the layers were separated. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (0.619 g) as colorless crystals (yield: 62.0%) 1H-NMR (400 MHz, CDCl3): delta(ppm) 3.23(2H, t, J=7.3Hz), 3.59(2H, t, J=7.3Hz), 7.31(2H, d, J=8.4Hz), 7.78(2H, d, J=8.4Hz).

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 72054-56-9.

Reference:
Patent; Eisai Co., Ltd.; US2002/19531; (2002); A1;,
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Electric Literature of 4210-32-6, 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. 4210-32-6, name is 4-(tert-Butyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

BuLi (2.5 M in hexanes, 0.46 mL, 1.14 mmol) wasadded to dry Pri2NH(127.5 mg, 1.3 mmol) in dry THF (2.0 mL) at -78¡ãCand the mixture was stirred at -78¡ãC for 10 min. Compound 41 (200 mg, 1.1 mmol) in dry THF (2.0 mL) was added and the mixturewas stirred for 1 h at -78¡ãC. 4-(1,1-Dimethylethyl)benzonitrile (180 mg, 1.1mmol) in dry THF (2.0 mL) was added and the mixture was stirred for 1 h at-78¡ãC, then at 20¡ãC for 16 h. Water (1.0 mL) was added. The mixturewas diluted with CH2Cl2, washed thrice with brine anddried. Evaporation and washing (EtOH) gave 13c (96.5 mg, 29percent) as a whitesolid: mp 204-206¡ãC; IR nmax3295, 1642 cm-1; 1H NMR ((CD3)2SO)(COSY) d 1.33 (9 H, s, CMe3),2.55 (3 H, s, 5-Me), 6.82 (1 H, s, 4-H), 7.35 (1 H, t, J = 7.6 Hz, 7-H), 7.51 (2 H, d, J= 7.6 Hz, Ph 3,5-H2), 7.54 (1 H, d, J = 7.2 Hz, 6-H), 7.75 (2 H, d, J= 7.6 Hz, Ph 2,6-H2), 8.06 (1 H, d, J = 8.0 Hz, 8-H), 11.48 (1 H, br, NH); 13C NMR((CD3)2SO) (HSQC / HMBC) d 18.75 (Me), 30.97 (CMe3), 34.44 (CMe3),99.60 (4-C), 124.56 (8-C), 124.86 (8a-C), 125.51 (Ph 3,5-C2), 125.72(7-C), 126.56 (Ph 2,6-C2), 131.44 (Ph 1-C), 133.15 (6-C), 133.60(4a-C), 136.69 (5-C), 139.84 (3-C), 151.87 (Ph 4-C), 162.97 (1-C); MS m/z 292.1686 (M + H)+ (C20H22NOrequires 292.1703).

The chemical industry reduces the impact on the environment during synthesis 4-(tert-Butyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Paine, Helen A.; Nathubhai, Amit; Woon, Esther C.Y.; Sunderland, Peter T.; Wood, Pauline J.; Mahon, Mary F.; Lloyd, Matthew D.; Thompson, Andrew S.; Haikarainen, Teemu; Narwal, Mohit; Lehtioe, Lari; Threadgill, Michael D.; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5891 – 5908;,
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Application of 6330-25-2, These common heterocyclic compound, 6330-25-2, name is 2-Cyano-N-methyl-acetamide, 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.

N -Methyl 2-amino-5-(2-(4-methoxyphenyl)ethyl)thiophene-3-carboxamide (TJ19). To a mixture of 4-(4-methoxyphenyl)butanal 6 (0.5 g, 2.805 mmol), 2-cyano-N- methylacetamide 8 (0.275 g, 2.805 mmol) and sulfur (0.090g, 2.805 mmol) in DMF (10 mL), NEt3(0.851 g, 8.451 mmol, 3 equiv) was added. After stirring the resulting mixture at 60C for 30 hrs, the reaction mixture was added to water (20 mL). Ethyl acetate (20 mL) was added and the organic solution was washed with distilled water (3 chi 20 mL), dried over MgS04, filtered, and then evaporated to dryness to afford the crude product mixture. Purification by column chromatography (silica, eluent CH2CI2- ethyl acetate 90-10) afforded TJ19 (0.27 g, 33%) as an off-white solid. 1H NMR (300 MHz, CDCI3) deltaEta 2.86 (m, 7H); 3.78(s, 3H); 5.57 (s, 2H); 6.64(s, 1 H); 6.81 (d, 2H); 7.06(d, 2H).

Statistics shows that 2-Cyano-N-methyl-acetamide is playing an increasingly important role. we look forward to future research findings about 6330-25-2.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; UNIVERSITA DEGLI STUDI DI FERRARA; BALZARINI, Jan; DEHAEN, Wim; THOMAS, Joice; LIEKENS, Sandra; ROMAGNOLI, Romeo; BARALDI, Pier Giovanni; WO2013/190137; (2013); A2;,
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Related Products of 6952-59-6, 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. 6952-59-6 name is 3-Bromobenzonitrile, 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 stirred mixture of aryl or heteroaryl halide(Br, I) (0.5 mmol), potassium mono ethyl malonate (0.75 mmol) in THF (10 mL) taken in a 30 mL microwave vial, was added Pd(OAc)2(5 mol%), Xantphos (5 mol %), MgCl2 (0.75), Et3N ( 0.75mmol), imidazole (1 mmol) followed by Co2(CO)8 (0.15mmol). The vial was sealed immediately and microwave irradiated at 90C for 30min. The reaction mixture was concentrated and diluted with ethyl acetate and water. The ethyl acetate layer was separated, dried over sodium sulphate and concentrated. The crude product obtained was purified by column chromatography to get the pure compound.

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

Reference:
Article; Baburajan, Poongavanam; Elango, Kuppanagounder P.; Tetrahedron Letters; vol. 55; 25; (2014); p. 3525 – 3528;,
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Reference of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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.

2-Fluoro-5-nitrobenzonitrile (500 mg, 3.01 mmol), 1H-1,2,3-triazole (228.68 mg, 3.31 mmol) and potassium carbonate (832.02 mg, 6.02 mmol) were added to MeCN (10 mL) and stirred at 25 C. for 16 h. The reaction mixture was filtered and the residue was washed with EtOAc (30 mL*2). The combined organic layers were concentrated under reduced pressure to afford a crude yellow solid, which was purified by FCC (petroleum ether/ethyl acetate from 100:0 to 70:30) to afford the title compound (600 mg, 92.6%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) 6=8.72 (d, J=2.6 Hz, 1H), 8.55 (dd, J=2.4, 9.0 Hz, 1H), 8.42 (d, J=9.3 Hz, 1H), 8.03 (s, 2H).

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
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