Tag: M.W=200-300

Reference of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-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.

A 48 mL pressure vessel containing 2-bromo-4-fluorobenzonitrile (1.00 g, 5.00 mmol), 2-pyrrolidinone (0.46 mL, 6.00 mmol), Cs2CO3 (2.28 g, 7.0 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (xantphos) (0.231 g, 0.40 mmol) in dioxane (6 mL) was degassed with argon for 15 min. Pd2dba3 was introduced and the reaction mixture heated at 105 C. for 48 h. The mixture was cooled, diluted with ethyl acetate or dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and subjected to column chromatography on silica gel with hexanes:ethyl acetate (3:7) gradient as the eluent to afford the title compound as a white solid (0.887 g, 87% yield): 1H NMR (400 MHz, CDCl3) delta ppm: 7.69 (1H, dd, J=5.8, 8.6 Hz), 7.22 (1H, dd, J=2.5, 9.6 Hz), 7.07 (1H, ddd, J=2.5, 7.6, 8.6 Hz), 3.96 (2H, t,. J=7.0 Hz), 2.62 (2H, t, J=8.1 Hz), 2.30-2.22 (2H, m); LCMS (+ESI, M+H+) m/z 205.

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-4-fluorobenzonitrile, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, 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 17216-62-5, category: nitriles-buliding-blocks

(a) 4-Cyano-2(R,S)-alpha-naphthylmethylbutyric acid 2.13 g of 2-cyanoethylmalonic acid diethyl ester are added to a suspension of 0.48 g of sodium hydride dispersion in 25 ml of DMF. The reaction mixture is stirred for 2 hours at 80 and then, at room temperature, 1.77 g of alpha-chloromethylnaphthalene in 5 ml of DMF are added. The mixture is further stirred for 16 hours at 50 and then concentrated by evaporation. The residue is dissolved in ethyl acetate, washed with 0.1N hydrochloric acid and water, dried over sodium sulphate and concentrated by evaporation, leaving 2-cyanoethyl-alpha-naphthylmethylmalonic acid diethyl ester.

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, Diethyl 2-(2-cyanoethyl)malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ciba-Geigy Corporation; US4727060; (1988); A;,
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Reference of 5866-98-8, These common heterocyclic compound, 5866-98-8, name is 2,6-Dichloro-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.

Example 30 Preparation of 6-Chloro-5-cyano-7-nitro-1,4-dihydroquinoxaline-2,3-dione To a stirred solution of 2,6-dichloro-3-nitrobenzonitrile (3.935 g, 18.13 mmol, Lancaster, used as received) in DMF (25 mL) at 70 C., an aqueous solution of sodium glycinate (1.760 g, 18.13 mmol, Aldrich, used as received) in water (25.0 mL) was added dropwise. The resulting solution was stirred at 70 C. for 48 h. The suspension was cooled to room temperature and the precipitated yellow solid was filtered, washed with chloroform (20 mL), and dried under vacuum to furnish 2.020 g (44%) of pure (1 H NMR) N-(3′-chloro-2′-cyano-6′-nitro)phenylglycine as a yellow powder. 1 H NMR (DMSO-d6): delta3.888 (d, 2H, J=3.9 Hz), 6.857 (d, 1H, J=9.0 Hz).

Statistics shows that 2,6-Dichloro-3-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 5866-98-8.

Reference:
Patent; State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of Oregon, Eugene Oregon; Acea Pharmaceuticals, Inc.; The Regents of the University of California; US5631373; (1997); A;,
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Synthetic Route of 4592-94-3, 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 4592-94-3 as follows.

General procedure: A microwave tube was charged with ketonitrile (2.0 mmol), methanol (1 mL), and hydrazine monohydrate (2.6 mmol) and subjected to microwave irradiation (100 W, 150 C) for 5 minutes. Volatiles were subsequently removed under reduced pressure. The residue was purified by either trituration with cold methanol or cyclohexane, or by using column chromatography to give the final product.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kelada, Mark; Walsh, John M. D.; Devine, Robert W.; McArdle, Patrick; Stephens, John C.; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 122 – 1228;,
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Adding a certain compound to certain chemical reactions, such as: 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, 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 1835-65-0, category: nitriles-buliding-blocks

EXAMPLE 45 Synthesis of Tetrafluoro-1,3-diiminobenz[f]isoindoline Anhydrous ammonia was slowly bubbled through a stirred mixture of tetrafluorophthalonitrile (2.0 g), 25percent sodium methoxide in methanol (2.3 ml), and dry 1-butanol (10 ml) for 20 minutes. With continued ammonia introduction, the mixture was refluxed for 1 hour. After the resultant had cooled, the solvent was removed under vacuum with a rotary evaporator. The residue was treated with ether (50 ml) and the product was collected by filtration, washed sequentially with water (10 ml), and ether (10 ml), vacuum dried and weighed (0.45 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4,5,6-Tetrafluorophthalonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Buechler, Kenneth F.; Noar, Joseph B.; Tadesse, Lema; US2002/61602; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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 4592-94-3, Computed Properties of C9H6BrNO

1.0 g (2.1 mmol) of N(4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolane-2-yl)- 1 -tosyl- 1 H-pyffolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide prepared from the reaction formula 3 above was dissolved in DMF/H 20 = 2:1 solution, and then 0.6 g (2.5 mmol) of 3-(4-bromophenyl)-3-oxopropanenitrile, 0.2 g (0.2 mmol) of Pd(PPh ) and 0.15 mL of 2M K 2C0 aqueous solution were inserted thereinto and stuffed at 100 – 110C for 2 hours. Once the reaction was completed, the said mixture was cooled down at room temperature, then water was added thereto, and then an extraction using ethyl acetate was performed. After that, a solution extracted therefrom was dried by means of magnesium sulfate anhydrous and concentrated under reduced pressure, from which a residue was accordingly obtained. The residue was separated via NH-silica gel column chromatography (n-hexane / ethyl acetate = 5: 1), and N(4-(4-(2-cyanoacetyl)phenyl)- 1 -tosyl- 1 H-pyrrolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide was synthesized. A synthesized material was dissolved in MeOH/THF (1:1) solution, and then 2N sodium hydroxide aqueous solution was added thereto and stirred at 30 – 40C for 4 hours. Once the reaction was completed, the said mixture was cooled down to room temperature, and saturated ammonium chloride aqueous solution was added thereto while being stirred. A produced solid was filtered out, and finally a product, i.e., N(4-(4-(2-cyanoacetyl)phenyl)- 1 H-pyrrolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide was accordingly obtained.MS(ESI+) mlz 345 (M+H) +

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, 3-(4-Bromophenyl)-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CJ HEALTHCARE CORPORATION; LEE, Hyuk Woo; JI, Mi Kyung; KIM, Seung Chan; YU, Ha Na; JUNG, Soo Yeon; PARK, Ji-Yeon; LEE, Ye-Lim; LEE, Ho-Youl; KI, So Young; KIM, Dongkyu; KIM, Myeongjoong; (410 pag.)WO2019/78619; (2019); A1;,
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Reference of 4592-94-3, 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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3-(4-bromophenyl)-3-oxopropanenitrile (1.0 g, 4.5 mmol) in THF (89 mL) was heated to reflux. Borane-THF complex (13 mL of 1 M solution, 13 mmol) was added dropwise. After 3.5 h the mixture was cooled to room temperature, then MeOH (20 mL) was added. The volatiles were evaporated to give a white residue, which was then dissolved in MTBE. The clear solution was treated with a 1 M ethereal HCl solution. The solvents were evaporated and the residue was partitioned between water and DCM. The organic phase was set aside. The aqueous phase was neutralized with a 50% aqueous sodium hydroxide solution, and then extracted with DCM (thrice). The combined organic phase was washed with brine and dried over sodium sulfate. The solvent was evaporated to give the title compound in impure form as a colorless oil (0.85 g) which was used without further purification. Exact mass calculated for C9H12BrNO: 229.0, found: LCMS m/z = 230.3 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 3-(4-Bromophenyl)-3-oxopropanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/58300; (2009); A1;,
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Reference of 179898-34-1, These common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-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.

Under argon, 3.60 g (18.0 mmol) of 3-bromo-5-fluorobenzenecarbonitrile, 5.03 g (19.8 mmol) of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane and 5.30 g (54.0 mmol) of potassium acetate are provided in 72 ml of degassed 1,4-dioxane/DMSO (10/1), and 441 mg (0.54 mmol) of 1,1′-bis(diphenylphosphine)ferrocenedichloropalladium(II)/dichloromethane complex are added. The mixture is stirred at 90 C. overnight. Water is subsequently added, the phases are separated, the aqueous phase is extracted with ethyl acetate and the combined organic phases are concentrated. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1). 4.48 g (92% of theory) of the title compound are obtained.1H-NMR (400 MHz, DMSO-d6): delta=8.01 (ddd, 1H), 7.82 (s, 1H), 7.70 (ddd, 1H), 1.32 (s, 12H).GC-MS (Method 11): Rt=4.94 min; MS (EIpos): m/z=247 [M]+.

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AiCuris GmbH & Co. KG; US2012/22059; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, 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 179898-34-1, HPLC of Formula: C7H3BrFN

1003751 Step A: 3-fluoro-5-formylbenzonitrile: A solution of 3-bromo-5- fluorobenzonitrile (5.00 g, 25.0 mmol) in dry THF (25 mL) was cooled to 0 C and 2M iPrMgCl (15.0 mE, 30.0 mmol) in TUF was added dropwise over 5 minutes. The mixture was stirred at 0 C for 15 minutes then at ambient temperature for 1 hour. The mixture was cooled to 0 C and dry DMF (5.81 mL, 75.0 mmol) was added. The mixture was stirred for 17 hours during which time the temperature reached ambient temperature after 2 hours. The mixture was added to ice water (150 mE) and Et20 (100 mE). The biphasic mixture was stirred and treated with 6M HC1 to aqueous pH=3. The organic layer was removed and the aqueous layer extracted with Et20 (2X). The combined Et20 fractions were washed with saturated NaC1 and dried over MgSO4/activated carbon. The dried solution was filtered through a Si02 plug eluting with Et20. The filtrate was concentrated to give the title compound as a yellow solid that was dried in vacuum (3.68 g, 99%). ?H NMR (CDCI3) 8 10.0 (s, 1H), 8.00 (s, 1H), 7.81- 7.86 (m, 111), 7.62-7.67 (m, 1H).

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:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven Wade; BLAKE, James F.; BRANDHUBER, Barbara J.; JIANG, Yutong; KERCHER, Timothy; WINSKI, Shannon L.; WO2014/78372; (2014); A1;,
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Application of 101184-73-0, 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. 101184-73-0, name is 2-(4-Bromophenyl)-2-methylpropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-(4-Bromophenyl)-2-methylpropylamine Prepared from alpha,alpha-dimethyl-(4-bromo)phenylacetonitrile (16 g, 0.0676 mol) using the method of description 4 to afford the title compound as the hydrochloride salt (16.87 g, 89%). 1H NMR (CDCI3) delta: 1.23 (6H, s), 2.89 (2H, s), 7.27 (2H, d, J=9 Hz), 7.43 (2H, d, J=9 Hz), 7.77 (3H, br s).

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-Bromophenyl)-2-methylpropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SmithKline Beecham p.l.c.; US6358974; (2002); B1;,
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