Tag: M.W=200-300

These common heterocyclic compound, 79630-23-2, name is 3-Bromo-4-fluorobenzonitrile, 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. Recommanded Product: 3-Bromo-4-fluorobenzonitrile

(Step 1) A suspension of 3-bromo-4-fluorobenzonitrile (0.851 g, 4.26 mmol), tetraethyltin (2.00 g, 8.51 mmol) and tetrakis(triphenylphosphine)palladium (98.4 mg, 0.0851 mmol) in HMPA (4 mL) was stirred at 60 C. for 15 hrs. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the concentrated residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give 3-ethyl-4-fluorobenzonitrile as a pale-yellow oil (1.25 g, crude).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
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Application of 89642-49-9, These common heterocyclic compound, 89642-49-9, name is 4-Bromo-3-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.

15.18 g (52.85 mmol) of 9-phenyl-9H-carbazole-3-yl-boronic acid, 10 g (44.04 mmol) of 4-bromo-3-nitrobenzonitrile, and 0.05 percent by weight (wt %) of a palladium catalyst were dissolved in 25 ml of toluene, 25 ml of 2 molar (M) potassium carbonate was added thereto, and the resulting reaction solution was stirred for 24 hours. After completing the reaction, the resulting reaction solution was extracted using chloroform to remove a solvent therefrom. Then, the resulting solid product was dried. 3 equivalents of triphenylphosphine were added thereto, and the mixture was stirred in dichlorobenzene for 12 hours at a temperature of 160 C. After completing the reaction, 100 ml of methanol was slowly added to the mixture, to thereby filter the resulting reaction solution. The filtered crude product obtained therefrom was dried and purified by column chromatography with a mixture of dichloromethane and hexane as an eluent, thereby obtaining 4.87 g (yield: 31%) of Intermediate 4. The structure of the synthesized compound was identified using a MALDI-TOF mass spectrometer. (0347) MALDI-TOF (calculated: 357.1 g/mol, measured: [M+H]+=358 g/mol)

Statistics shows that 4-Bromo-3-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 89642-49-9.

Reference:
Patent; SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.; Jeon, Soonok; Numata, Masaki; Lee, Saeyoun; Miyazaki, Hiroshi; Son, Jhunmo; Sim, Myungsun; Lee, Namheon; Ihn, Sooghang; (116 pag.)US10510966; (2019); B2;,
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Related Products of 160892-07-9, 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. 160892-07-9 name is 5-Bromoisophthalonitrile, 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.

5-bromoisophthalonitrile (1 g, 48.3 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2,1-jk]carbazole (1.77 g, 48.3 mmol) were dissolved in 1,4dioxane (50 ml). K2CO3 (1.34 g, 96.6 mmol) was dissolved in water and poured into the mixture. The reaction mixture was stirred with N2 bubbling for 30 min and refluxed overnight. After cooling to room temperature, the mixture was filtered and diluted with methylene chloride and washed with distilled water. The organic layer was dried over anhydrous MgSO4 and evaporated in vacuum. And then, the product was isolated by column chromatography on a silica gel.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisophthalonitrile, and friends who are interested can also refer to it.

Reference:
Patent; RESEARCH & BUSINESS FOUNDATION SUNGKYUNKWAN UNIVERSITY; LEE, Junyeob; IM, Yirang; (37 pag.)US2018/114924; (2018); 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. 145498-86-8, name is Methyl 2-(cyanomethyl)-3-methoxybenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 145498-86-8

Into a 500 mL 3-neck round bottom flask was added 10 g (61.75 mmol) of 2-bromomethyl, 3-methoxy methyl benzoate, 4.0 g (81.6 mmol) of NaCN, 0.30 g (2 mmol) of NaI, 100 mL of CH3CN, and 50 mL of DMF. The reaction mixture was heated and refluxed for 10 hours. The precipitate (NaBr) was filtered off, and the solution was concentrated on an evaporator. 300 mL of water and 200 mL of ether were added and then shaken in a separatory funnel. The water was extracted twice with 100 mL of ether. The ether fractions were dried over MgSO4, and concentrated to yield methyl 3-methoxy-2-cyanomethylbenzoate (95-100% yield). This ester (0.053 mmol, 10.51 g) was stirred vigorously in 100 mL of CH3OH. Ba(OH)2 H2O (0.079 mmol, 14.97 g) was added and the mixture stirred at room temperature overnight. The CH3OH was removed on a rotary evaporator. 150 mL of water, 200 mL of CH2Cl2, and 50 mL of 6N HCl were added, and then stirred in a flask to dissolve all residues. The mixture was transferred to a separatory funnel, acidified with 6N HCl to pH 1-2. The CH2Cl2 phase was separated and the aqueous phase extracted twice with 50 mL of CH2Cl2. The CH2Cl2 extracts were combined, dried over MgSO4 and charcoal, filtered, and evaporated to yield 8.8 g of a white solid, 2-cyanomethyl-3-methoxybenzoic acid, (87%). Methyl 3-methoxy-2-cyanomethylbenzoate: 1H NMR (CDCl3, 300 MHz) delta (ppm): 7.6 (d, 1H), 7.4 (t, 1H), 7.1 (d, 1H), 4.18 (s, 2H), 3.94 (s, 3H), 3.926 (s, 3H). TLC (1:1 ethyl acetate: hexane) 0.55. 2-Cyanomethyl-3-methoxybenzoic acid: 1H NMR (300 Mhz, CDCl3) delta (ppm): 7.55 (d, 1H), 7.45 (t, 1H), 7.3 (d, 1H), 4.121 (d, 2H), 3.91, (s, 3H). TLC (1:1 ethyl acetate: hexane

The synthetic route of 145498-86-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hormann, Robert Eugene; Potter, David W.; Chortyk, Orestes; Tice, Colin M.; Carlson, Glenn Richard; Meyer, Andrew; Opie, Thomas R.; US2006/20146; (2006); 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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-3-fluorophenylacetonitrile

General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetonitriles 1 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.), and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture DBU (456 mg, 3 mmol, 3.0 equiv.) was added. The mixture was stirred for 12 hours at room temperature, and then to the mixture was added saturated ammonium chloride solution (25 mL). The resulting mixture was extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 2 was purified using silica gel column chromatography using an appropriate eluent.

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 499983-13-0.

Reference:
Article; Zhou, Mingwei; Hu, Yimin; En, Ke; Tan, Xuefei; Shen, Hong C.; Qian, Xuhong; Tetrahedron Letters; vol. 59; 14; (2018); p. 1443 – 1445;,
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Synthetic Route of 51632-29-2, 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 51632-29-2 as follows.

3-phenoxyphenylacetonitrile was added to a 25 ml Schlenk reaction tube under a nitrogen atmosphere.(0.4 mmol), dimethylamine borane complex (1 equivalent), potassium t-butoxide (1.5 eq.), deuterated N,N-dimethylformamide (2 ml), rubber stopper on the reaction tube After being placed in an oil bath, the reaction was carried out at 80 C for 7 h, and the end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography, and the eluent was petroleum ether / ethyl acetate ( v: v = 10: 1), obtaining alpha-monodecylmethyl-3-phenoxybenzenepropionitrile;Then, under a nitrogen atmosphere, a 25 ml two-neck round bottom flask was charged with alpha-monodeuteromethyl-3-phenoxyphenylpropanenitrile (0.2 mmol), sodium hydroxide (1.5 mmol/ml), water (8 ml). Ethanol (2ml), burned in a round bottomThe bottle was placed in a rubber bath and placed in an oil bath. The reaction was refluxed at 110 C for 5 h. The end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. Petroleum ether / ethyl acetate (v: v = 5: 1) gave alpha-monodecylmethyl-3-phenoxyphenylpropionic acid, i.e., alpha-monodecylmethyl-fenofol.Product yield 80%, light yellow solid

According to the analysis of related databases, 51632-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; University of Science and Technology of China; Wang Yifeng; Xia Huimin; Zhang Fenglian; (10 pag.)CN108003004; (2018); A;,
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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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Chloro-4-(trifluoromethyl)benzonitrile

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

According to the analysis of related databases, 1813-33-8, the application of this compound in the production field has become more and more popular.

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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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. 97165-77-0, name is 3,5-Dibromobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 3,5-Dibromobenzonitrile

To a round bottom flask was added 20.0 g (77 mmol) of 3,5-dibromobenzonitrile and 13.2 g (77 mmol) of 1-naphthaleneboronic acid,1.8 g (2 mmol) of tetrakistriphenylphosphine palladium {Pd (PPh3) 4}21.2 g (153 mmol) of potassium carbonate,30 mL of water,100 ml of toluene and 100 ml of tetrahydrofuran were added and the mixture was refluxed for 12 hours.After completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure.Hexane, and dried to obtain 13.1 g of a white solid having a yield of 55.5%.

The synthetic route of 97165-77-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC Ltd.; Ryu Se-jin; Sim So-yeong; Lee Sang-hae; (39 pag.)KR101964677; (2019); B1;,
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Related Products of 950596-58-4, 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. 950596-58-4 name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, 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.

In the reaction flask was charged with 2-amino-4,5-bis (2-methoxyethoxy) – benzonitrile (37.01g, 0.139mol) and acetonitrile (185ml); added 3-ethynyl aniline salt acid (30.00g, 0.195mol), trifluoroacetic acid (17.43g, 0.152mol) and formamidine acetate (15.19g, 0.145mol) in the resultant mixture.The reaction mixture temperature was adjusted to reflux temperature of the solvent, and maintained in this condition for about 15 hours.At the end of the reaction, the temperature was adjusted to about 25 , the solvent was removed by vacuum distillation, and methyl ethyl ketone (430ml).(2 ¡Á 100ml) and water (2 ¡Á 100ml) the organic phase was washed with saturated sodium bicarbonate solution.The organic phase was collected and concentrated by vacuum distillation to a residue.The resulting crude product was suspended in ethyl acetate (450ml), and adding 37% hydrochloric acid solution (14.38g, 0.145mol), maintained at a temperature of 15 for about 30 minutes.The resulting solid was filtered, washed under vacuum at 45 C oven dried to obtain 36.02g erlotinib hydrochloride.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Guilin Hui Pak Biotechnology Co., Ltd.; M, Balatella; P, Palanza; M, Garbodi; G, Castaldi; (7 pag.)CN105541735; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 79463-77-7, name is Diphenyl N-cyanocarbonimidate, 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 79463-77-7, category: nitriles-buliding-blocks

[00606] 147A. l-(3-Chloro-2-fiuorophenyl)-N-[(10R,14S)-5-{[(lZ)- (cyanoimino)(phenoxy)methyl] amino } – 10-methyl-9-oxo-8 , 16- diazatricyclo[13.3.1.02’7]nonadeca-l(19),2(7),3,5,15,17-hexaen-14-yl]-5-methyl-lH- l,2,3-triazole-4-carboxamide: A mixture of Example 89 (Alternative, HC1 salt) (10 mg, 0.016 mmol), pyridine (10.42 mu?, 0.129 mmol) and diphenyl cyanocarbonimidate (7.67 mg, 0.032 mmol) in 2-propanol (0.15 mL) was stirred in a pressure-tested vial at room temperature for 2 h. The reaction mixture was concentrated to give the product (11 mg, 99%) as an oily solid. MS(ESI) m/z: 692 (M+H)+.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Nitrile – Wikipedia,
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