Tag: M.W=200-300

Electric Literature of 57381-37-0,Some common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, molecular formula is C7H3BrClN, 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 35; 5-chloro-1-[5-chloro-2-(2-oxopyrrolidin-1-yl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride; (Step 1); To a solution (139 ml) of 2-bromo-5-chlorobenzonitrile (15.0 g), pyrrolidin-2-one (7.90 ml) and cesium carbonate (45.2 g) in 1,4-dioxane were added tris(dibenzylideneacetone)dipalladium (1.59 g) and 4,5-bis(biphenylphosphino)-9,9-dimethylxanthine (2.0 g) at room temperature under a nitrogen atmosphere, and the mixture was heated under reflux for 3 hr. The mixture was allowed to cool to room temperature, and extracted with ethyl acetate and water. The organic layer was filtered through celite, and washed with ethyl acetate. The filtrate was dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (ethyl acetate_hexane=1:10?1:1) to give 5-chloro-2-(2-oxopyrrolidin-1-yl)benzonitrile (12.5 g) as yellow crystals. 1H NMR (400 MHz, CD3OD) delta ppm 2.24-2.31 (2H, m) 2.62 (2H, t, J=8.0 Hz), 3.94 (2H, t, J=6.8 Hz) 7.39 (1H, d, J=9.2 Hz) 7.60 (1H, dd, J=2.4, 8.8 Hz) 7.67 (1H, d, J=2.4 Hz).

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/270393; (2009); A1;,
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Synthetic Route of 1835-65-0, A common heterocyclic compound, 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, molecular formula is C8F4N2, 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.

COMPARATIVE EXAMPLE 2Preparation of a Vanadyl Phthalocyanine CompoundlOg of 3,4,5,6-tetrafluorophthalonitrile, lOg ofthiophenol and 7 g of potassium fluoride were added to 3 neck flask equipped with a reflux apparatus, and then 30 ml of acetonitrile was added as a solvent, and the mixture was reacted withstirring for 12 hours at room temperature. Afier reaction was completed, 7 g of 2,6-dimethylphenol and 4 g of potassium fluoride were added to the reacting solution, and then refluxed for 8 hours. Afier reaction was completed, the solution was distilled with a vacuum distillet 20 g of crude reactantsobtained as above were added to 3 neck flask equipped with a reflux apparatus, and refluxed with 2 g of vanadium trichloride, 2 g of 1-octanol and 30 g of benzonitrile for 8 hours. Afier reaction was completed, the solution was distilled with a vacuum distiller to obtain a vanadyl (vanadium oxide) phthalocyaniene (VOPc: Oxo-Vanadium Phthalocyanine)30 based precursor compound VOPc(PhS)8{2,6-(CH3)2PhO}4F4. 10 g of the vanadyl phthalocyanine-based precursor compound and 50 ml of cyclohexylamine were added to 3 neck flask equipped with a reflux apparatus, and reacted for 8 hours at 60¡ã C. Afier reaction was completed, the reactingsolution was concentrated in vacuum to obtain a vanadyl phthalocyanine compound VOPc(PhS)8{2,6-(CH3)2PhO}4 (C5H11NH)4 (Ph=phenyl; in the formula 2 below, A2, A3, A5, A7, A10, A11, A14 and A15 are PhS; A1, A5, A9 and A13 are {2,6-(CH3)2PhO}; and A4, A8, A12 and A15 are C5H11NH)represented by the formula 2

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.; Kang, Ju-Sik; Park, Jeong-Ho; Chang, Yu-Mi; US9158048; (2015); B2;,
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Application of 846023-24-3, The chemical industry reduces the impact on the environment during synthesis 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, I believe this compound will play a more active role in future production and life.

EXAMPLE 44 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{4-methoxy-3-[3-(4-methylpiperazin-1-yl)-propoxy]-phenylamino}-acrylamide To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (1.75 g, 6.75 mmol) in 8.2 mL of iso-propanol was added triethylorthoformate (1.5 g, 10.1 mmol). The mixture was heated to reflux. After 20 minutes, 4-methoxy-3-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenylamine in 20 mLs of iso-propanol was added dropwise so as to maintain reflux. After 26 hours, the reaction was cooled to room temperature and the suspended solids were filtered. The solids were rinsed with iso-propanol until effluent was colorless. The yellow solid was dried in vacuo to give 3.45 g (93%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{4-methoxy-3-[3-(4-methylpiperazin-1-yl)-propoxy]-phenylamino}-acrylamide as a mixture of isomers. 1H NMR (300 MHz, CDCl3) delta 11.35 (br d, 1H), 8.17 (m, 2H), 7.76 (d, 1H), 7.41 (s, 1H), 6.88 (m, 1H) 6.69 (m, 2H), 4.10 (t, J=7 Hz, 2H), 3.96 (s, 3H), 3.87 (s, 3), 2.55 (t, J=7 Hz, 2H), 2.48 (m, 8H), 2.29 (s, 3H), 2.06 (m, 2H); MS (ES) m/z548.1 (M+) Analysis for C10H14ClNO2; Calcd: C, 55.69; H, 6.54; N, 6.49. Found: C, 55.49; H, 6.59; N, 6.32.

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-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth Holdings Corporation; US2005/43537; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile, 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 17823-40-4, Recommanded Product: 17823-40-4

A mixture of (1,2-dihydroacenaphthylen-5-yl)boronic acid (1.6 g, 8 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (1.0 g, 3.9 mmol), Pd2(dba)3 (0.18 g, 0.20mmol), SPhos (0.16 g, 0.4 mmol), K3PO4 (2.0 g, 8.7 mmol) in toluene (50 mL) was degassed and heated at about 120 C for about 16 hours. After filtered off precipitate and washed with toluene, the filtrate was purified by flash column using eluents of hexane to hexane/dichloromethane (7:3). Removal of solvent give awhite solid (Compound 9) (0.54 g, in 42% yield).

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-Bromo-2,3,5,6-tetrafluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, SHIJUN; BASIAGO, ADAM; (86 pag.)JP2016/526025; (2016); 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. 691877-03-9, name is 3-Bromo-5-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Bromo-5-(trifluoromethyl)benzonitrile

43-2 (50 mg, 0.200 mmol) was dissolved in THE (1 mL) before 1M Borane in THF (1 ML) was added. The mixture was stirred at RT overnight before concentrated IN VACUO. The residue was redissolved in a solution of 1% HCl (4N in dioxane) in methanol and heated at 50 C overnight. Solvent was stripped off and redissolved in 1% HCl in methanol. This process was repeated three times to get ride of excess borane and yield crude 43-3 (50 mg, 98.4%). LC-MS: MW calculated 252.97, found 253.8.

According to the analysis of related databases, 691877-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2004/41279; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 90433-20-8, name is 2-(3-Bromophenyl)-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 90433-20-8, Recommanded Product: 2-(3-Bromophenyl)-2-methylpropanenitrile

General procedure: To a mixture of compound 5 (2.00 g, 12.3 mmol), X-Phos (0.292 g, 0.613 mmol), sodium tert-butoxide (2.94 g, 30.6 mmol) and tris(dibenzylidineacetone)dipalladium (0.224 g, 0.245 mmol) in 1,4-dioxane (25 mL) was added 4-bromoanisole (1.6 mL, 12.9 mmol) and heated to 100 C for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and concentrated in vacuo. The residue was powdered from diethyl ether to give the title compound (2.02 g, 61%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3-Bromophenyl)-2-methylpropanenitrile, and friends who are interested can also refer to it.

Reference:
Article; Mochizuki, Michiyo; Kori, Masakuni; Kono, Mitsunori; Yano, Takahiko; Sako, Yuu; Tanaka, Maiko; Kanzaki, Naoyuki; Gyorkos, Albert C.; Corrette, Christopher P.; Aso, Kazuyoshi; Bioorganic and Medicinal Chemistry; vol. 24; 19; (2016); p. 4675 – 4691;,
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Reference of 13338-63-1,Some common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, molecular formula is C11H13NO3, 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: In the first synthetic step (step a, Scheme 1), a series of (Z)-substituted diarylacrylonitrile analogues were synthesized by reacting substituted benzyl carbaldehydes with their corresponding substituted phenylacetonitriles in 5% NaOMe in methanol. The reaction mixture was stirred at room temperature for 2-3 h for the reaction to complete and the final product precipitated of the solution. The precipitate was filtered, washed with water and dried to yield the final compound in yields ranging from 70 to 95% (Scheme 1) [16].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5-Trimethoxyphenylacetonitrile, its application will become more common.

Reference:
Article; Madadi, Nikhil R.; Penthala, Narsimha R.; Howk, Kevin; Ketkar, Amit; Eoff, Robert L.; Borrelli, Michael J.; Crooks, Peter A.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 123 – 132;,
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Related Products of 57381-49-4, 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. 57381-49-4 name is 2-Bromo-4-chlorobenzonitrile, 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.

General procedure: General Method 2A: Suzuki Coupling A flask which had been dried by heating and flushed with argon was initially charged with 1.0 eq. of the appropriate boronic acids, 1.0 eq. of the aryl bromide or aryl iodide, 3.0 eq. of potassium carbonate and 0.1 eq. of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/monodichloromethane adduct or tetrakis(triphenylphosphine)palladium(0). The flask was then evacuated three times and in each case vented with argon. Dioxane (about 6 ml/mmol) was added, and the reaction mixture was stirred at 110 C. for a number of hours until substantially complete conversion had been achieved. The reaction mixture was then filtered through Celite and the filtrate was concentrated under reduced pressure. Water was added to the residue. After addition of ethyl acetate and phase separation, the organic phase was washed once with water and once with saturated aqueous sodium chloride solution, dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure. The crude product was then purified either by means of normal phase chromatography (eluent: cyclohexane/ethyl acetate mixtures or dichloromethane/methanol mixtures) or preparative RP-HPLC (water/acetonitrile gradient or water/methanol gradient). Example 2.1B 4-Chloro-2-(2,5-dimethoxypyridin-4-yl)benzonitrile According to General Method 2A, 7.87 g (95% purity, 40.86 mmol) of 2,5-dimethoxypyridin-4-ylboronic acid were reacted with 8.85 g (40.86 mmol) of 2-bromo-4-chlorobenzonitrile in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct. Yield: 6.23 g (92% purity, 51% of theory). LC/MS [Method 1]: Rt=1.08 min; MS (ESIpos): m/z=275 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; HILLISCH, Alexander; STRAssBURGER, Julia; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; BUCHMUeLLER, Anja; GERDES, Christoph; SCHAeFER, Martina; TELLER, Henrik; JIMENEZ NUNEZ, Eloisa; SCHIROK, Hartmut; KLAR, Juergen; LOBELL, Mario; (39 pag.)US2017/283412; (2017); A1;,
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Synthetic Route of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Add 5-bromo-2-fluoro-benzonitrile (0.5 g, 2.5 mmol), benzophenone imine (0.543 g, 3 mmol), (¡À)-2,2′-bis(diphenylphosphino)-l,l’-binaphthalene (BetaGammaNuAlphaRho, 60 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 50 mg, 0.05 mmol], and Cs2C03 (1.6 g, 4.9 mmol) in 1,4-dioxane (20 mL). Stir the reaction under N2 at 110C for 16 hrs. Cool to room temperature, filter the solid, and concentrate the filtrate to give the crude product. Purification by chromatography (silica gel, EtOAc_PE=l :3) affords the title compound (0.78 g, 99%). MS: (M+1): 301.

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

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHANG, Deyi; ZHANG, Ruihao; ZHONG, Boyu; SHIH, Chuan; WO2014/418; (2014); A1;,
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Reference of 57381-37-0, These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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 stirred solution of 2-bromo-5-chloro-benzonitrile (10 g, 46 mmol) in THF (200 mL)at 0C, was added MeMgBr (77 mL, 230 mmol) dropwise. The reaction mixture wasallowed to warm up to room temperature and stuffed for 2 hours. Ti(Oi-Pr)4 (13 g, 46mmol) was added and the solution was stuffed for another 16 hours before it was quenchedwith aq. HC1 solution and washed with EtOAc. The aqueous phase was adjusted to pH 10 with aq. NaOH solution, and exacted with EtOAc (3 x 100 mL). The combined organic layers were concentrated to give a crude title product (3.8 g, yield 33%) as oil, which was used directly in the next step without further purification. MS: 249.30 (M+Hj

The synthetic route of 57381-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191340; (2014); A1;,
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