Tag: M.W=100-200

These common heterocyclic compound, 60702-69-4, name is 2-Chloro-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. 60702-69-4

To a solution of (4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one 7 33 (7.00 g, 60.8 mmol) in THF (120 mL) was added sodium bis(2-methoxyethoxy)aluminium dihydride (70% in toluene, 59.7 mL, 215 mmol) slowly at 5 C. After stirring at 70 C for 3 h, the reaction mixture was cooled to 5 C followed by addition of sodium carbonate decahydrate (26.1 g, 91.2 mmol). The mixture was stirred at room temperature for 16 h, diluted with THF, and the precipitate was filtered off. The filtrate was concentrated in vacuo, and the residue was dissolved in DMSO (80 mL). To the solution was added lithium carbonate (8.99 g, 122 mmol) and 2-chloro-4-fluorobenzonitrile (9.46 g, 60.9 mmol), and the mixture was stirred at 100 C for 1 h. The mixture was diluted with EtOAc and H2O, and the organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to give 10 (10.7 g, 74%) as a colorless solid. 1H NMR (300 MHz, CDCl3) delta: 1.18 (3H, d, J = 6.6 Hz), 1.82 (1H, d, J = 5.5 Hz), 2.01-2.14 (1H, m), 2.25-2.35 (1H, m), 3.19-3.28 (1H, m), 3.43-3.51 (1H, m), 3.89-3.98 (1H, m), 4.43-4.52 (1H, m), 6.43 (1H, dd, J = 8.9 and 2.4 Hz), 6.56 (1H, d, J = 2.4 Hz), 7.42 (1H, d, J = 8.9 Hz). MS (ESI) m/z 237 [(M+H)+].

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 60702-69-4.

Reference:
Article; Yamamoto, Satoshi; Kobayashi, Hiromi; Kaku, Tomohiro; Aikawa, Katsuji; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 70 – 83;,
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These common heterocyclic compound, 332-25-2, name is 4-(Trifluoromethoxy)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. 332-25-2

The 4 – trifluoro nitrile (187 mg, 1mmol), butyric aldehyde wo (96 mg, 1 . 1mmol), [Cp * IrCl2]2(8 mg, 0 . 01mmol, 1 muM percent), toluene (1 ml) are added to the 25 ml Schlenk reaction bottle. The mixture 100 ¡ãC reaction under 6 hours, cooling to room temperature. The benzyl alcohol (140 mg, 1 . 3mmol) and cesium carbonate (65 mg, 0.2 equiv.) is added to the bottle in the reaction, the mixture 130 ¡ãC then continue to react under 12 hours, cooling to room temperature. The solvent is removed by rotary evaporation, then through the column chromatography (developing solvent: ethyl acetate/petroleum ether) to obtain the pure target compound, yield: 82percent.

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 332-25-2.

Reference:
Patent; Nanjing University of Science and Technology; Li Feng; Wang Nana; Zou Xiaoyuan; (15 pag.)CN105016938; (2017); B;,
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Adding a certain compound to certain chemical reactions, such as: 23842-82-2, name is 2-Amino-5-methoxybenzonitrile, 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 23842-82-2, 23842-82-2

Ketone (¡À)-5 (95 mg, 0.63 mmol) was dissolved in dry 1,2-dichloroethane (1 mL). AnhydrousAlCl3 (126.5 mg, 0.95 mmol) and 7 (121 mg, 0.79 mmol) were added to this solution. The mixturewas stirred under MW (50W, 300 psi, high stirring) conditions at 95 C for 2 h. After the completionof the condensation, mixture of THF/H2O (7.5 mL, 2:1) was added, followed by 2 M aq. solution ofNaOH adjusting pH to 8-9. The resulting mixture was stirred for 30 min. The organic and aqueousphases were separated and the aqueous one was washed with dichloromethane (2 8 mL). Combinedorganic layers were dried over anhydrous Na2SO4 and the solvent was removed under reducedpressure. The crude product was purified by column chromatography (CH2Cl2/MeOH/TEA, 95:5:1).Compound (¡À)-1 (142 mg) was obtained in 80% yield in two steps as a white 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-Amino-5-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mezeiova, Eva; Korabecny, Jan; Sepsova, Vendula; Hrabinova, Martina; Jost, Petr; Muckova, Lubica; Kucera, Tomas; Dolezal, Rafael; Misik, Jan; Spilovska, Katarina; Pham, Ngoc Lam; Pokrievkova, Lucia; Roh, Jaroslav; Jun, Daniel; Soukup, Ondrej; Kaping, Daniel; Kuca, Kamil; Molecules; vol. 22; 8; (2017);,
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658-99-1, 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. 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below.

Under protective gas (argon), 125 mg (1.11 mmol) of potassium tert-butoxide were added to 1.006 g (5.55 mmol) of methyl (2E)-3-(5-fluoropyridin-3-yl)acrylate and 0.850 g (5.55 mmol) of (3,4-difluorophenyl)acetonitrile in 45.0 ml of toluene and 2 ml of DMF, and the mixture was stirred at 60 C. for 5 h. After removal of the solvent under reduced pressure, the residue was taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 1.050 g (57% of theory) of the diastereomeric methyl 4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoates.

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; Bayer CropScience Aktiengesellschaft; MOSRIN, MARC; JAKOBI, HARALD; DIETRICH, HANSJOERG; GATZWEILER, ELMAR; ROSINGER, CHRISTOPHER HUGH; SCHMUTZLER, DIRK; (66 pag.)US2017/290330; (2017); A1;,
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3939-09-1, Name is 2,4-Difluorobenzonitrile, 3939-09-1, 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.

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the mixture stirred at 90 C. for 3 h after which the mixture was filtered and the solvent removed. The resulting residue was adsorbed onto silica gel and intermediates 67 and 68 separated by flash chromatography, eluting with 0% to 30% ethyl acetate/hexanes. 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. Colorless needles (2.46 g, 18% yield) 1H NMR (500 MHz, CDCl3) delta: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. 4-(1H-1,2,4-Triazol-1-yl)-2-fluorobenzonitrile. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) delta: 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile and 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitrile. To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in THF (20 mL), and DMF (40 mL) was added 1,2,4-triazole sodium (6.3 g, 70 mmol) and the mixture was stirred at 90 C. for 3 h, filtered and concentrated. The residue was adsorbed onto Silica gel and purified by flash chromatography eluting with 0%-10%-30% EtOAc/hexanes to give the 4-triazolyl isomer as colorless needles (2.46 g, 18%) and the 2-substituted isomer as a white solid (0.7455 g, 6%). 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. 1H NMR (500 MHz, CDCl3) delta: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitrile. 1H NMR (500 MHz, CDCl3) delta: 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13.

Statistics shows that 2,4-Difluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 3939-09-1.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
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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. 3939-09-1, name is 2,4-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3939-09-1

4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile and 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. A solution of 2,4-difluorobenzonitrile (7.07 g, 50.8 mmol) and 3-methyl-1H-1,2,4-triazole (4.22 g, 50.8 mmol) in N,N-dimethylformamide (45 ml) was treated with powdered anhydrous potassium carbonate (10 g) and the resulting mixture was stirred at 22 C. for 18 h. The solid was then filtered and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The mixture containing the 2 and 4-triazolyl-benzonitriles was purified by a combination of chromatography on silica gel (elution gradient of ethyl acetate in hexane) and on reversed phase silica gel to give 1.86 g (18% yield) of 4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile and 0.526 g (5% yield) of 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. 4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate/hexanes). mp 117-118 C. 1HNMR 400 MHz (CDCl3) delta (ppm): 2.54 (3H, s, CH3), 7.24 (1H, m, CH), 7.62 (1H, dd, J=2.5 Hz and J=9.1 Hz, CH), 7.84 (1H, dd, J=5.6 Hz and J=8.6 Hz, CH), 8.82 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40; H, 3.49; N, 27.71. Found: C, 59.25; H, 3.32; N, 27.81. 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane). mp 120-121 C. 1HNMR 400 MHz (CDCl3) delta (ppm): 2.56 (3H, s, CH3), 7.30 (1H, dd, J=2.5 Hz and J=8.1 Hz, CH), 7.39 (1H, m, CH), 7.91 (1H, dd, J=5.5 Hz and J=8.6 Hz, CH), 8.06 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40; H, 3.49; N, 27.71. Found: C, 59.35; H, 3.70; N, 27.77.

The synthetic route of 3939-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
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21524-39-0, These common heterocyclic compound, 21524-39-0, name is 2,3-Difluorobenzonitrile, 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 3 -methyl- lH-pyrazole-4-carboxylic acid ethyl ester (1.25 g, 8.1 1 mmol), potassium carbonate (1.68 g, 12.16 mmol), 2,3-difluorobenzonitrile (1.08 mL, 9.73 mmol) in dimethylformamide (12 mL) is heated at 100C with the aid of a magnetic stirred. After 2.5 hr. the reaction mixture is treated with water and extracted with ethyl acetate. The organic layer is decanted, washed with brine, dried over magnesium sulfate and the solvent evaporated under reduced pressure to give 2.3 g of l-(2-cyano-6-fluoro- phenyl)-3 -methyl- lH-pyrazole-4-carboxylic acid ethyl ester (this compound is contaminated with the other pyrazole regioisomer in a ratio 75:25). MS (m/z): 274 (M+1). A capped vial is charged with ethyl l-(2-cyano-6-fluoro-phenyl)-3-methyl- pyrazole-4-carboxylate (1.97 g, 7.21 mmol) (contaminated with the other pyrazole regioisomer in a ratio of 75:25, 1,2-ethanediamine, N-methyl- (6 mL, 68.02 mmol) and phosphorus pentasulfide (229 mg, 1,01 mmol) and the mixture is stirred at 1 10C for 30 min and then allow to reach rt. Solvent is evaporated in vacuo and the residue purified by normal phase Isco chromatography using dichloromethane/2M ammonia in methanol from 95/5 to 85/15 as eluent to yield 2.1 1 g of ethyl l-[2-fluoro-6-(l-methyl-4,5- dihydroimidazol-2-yl)phenyl]-3-methyl-pyrazole-4-carboxylate (contaminated with the other pyrazole regioisomer in a ratio 75:25). MS (m/z): 331 (M+1). Potassium permanganate (1.58 g, 10 mmmol) and montmorillonite K- 10 (3.16 g) are grounded together in a mortar until a fine homogeneous powder is obtained.KMn04-montmorillonite K-10 (3.2 g, 6.78 mmol) is added portionwise to a solution of ethyl l-[2-fluoro-6-(l-methyl-4,5-dihydroimidazol-2-yl)phenyl]-3-methyl-pyrazole-4- carboxylate (1.12 g, 3.39 mmol) (contaminated with the other pyrazole regioisomer in a ratio 75:25) in acetonitrile (84.76 mL, 1.62 moles). The mixture is stirred at room temperature for 6.5 hr. and more KMn04-montmorillonite K-10 (0.8 g, 1.69 mmol) is added portionwise and the mixture stirred at room temperature overnight. Ethanol is added and stirred for additional 20 min. Then the reaction mixture is filtered through a short pad of celite and the solid material is washed with acetonitrile. The solvent is evaporated under reduced pressure and the crude mixture is purified normal phase Isco chromatography using ethyl acetate as eluent to yield 518 mg of l-[2-fluoro-6-(l- methylimidazol-2-yl)phenyl]-3-methyl-pyrazole-4-carboxylate (contaminated with the other pyrazole regioisomer in a ratio 75:25). MS (m/z): 329 (M+1).

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 21524-39-0.

Reference:
Patent; ELI LILLY AND COMPANY; BENITO COLLADO, Ana Belen; DIAZ BUEZO, Nuria; JIMENEZ-AGUADO, Alma Maria; LAFUENTE BLANCO, Celia; MARTINEZ-GRAU, Maria Angeles; PEDREGAL-TERCERO, Concepcion; TOLEDO ESCRIBANO, Miguel Angel; WO2011/60217; (2011); A1;,
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16532-79-9, 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. 16532-79-9, name is 4-Bromophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-Bromophenylacetonitrile (10.0 g, 51.0 mmol) in tetrahydrofuran (200 mL) was added slowly to a suspension of sodium hydride (60% in mineral oil, 6.0 g, 153 mmol) in tetrahydrofuran (400 mL) at room temperature over 30 minutes. After complete addition, methyl iodide (7.6 mL, 122 mmol) was added slowly over 30 minutes, maintaining the reaction temperature below 40 C. by occasional immersion into a water bath. The reaction was then stirred overnight at room temperature. The mixture was poured into water (500 mL) and extracted into ethyl acetate (2*300 mL). The combine organic layers were washed with brine (2*300 mL), dried over magnesium sulfate, filtered and concentrated. Crude purified on silica gel eluding with 2% ethyl acetate in hexanes) to give 2-(4-bromophenyl)-2-methylpropanenitrile (11 g, 96%) as a yellow oil. 1H NMR (300 MHz, CDCl3): delta ppm 1.70 (s, 6H), 7.35 (dd, 2H), 7.53 (dd, 2H).

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; pfizer Inc; US2010/197591; (2010); A1;,
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127946-77-4, Name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 127946-77-4, 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.

A mixture of example 9a) (850 mg, 2.74 mmol, Eq: 1.00), 1-aminocyclopropane- carbonitrile hydrochloride (422 mg, 3.56 mmol, Eq: 1.30), sodium 2-ethylhexanoate (705 mg, 4.24 mmol, Eq: 1.55) in water (3 ml) and THF (2.00 ml) was stuffed at 55 C for 18 h. To the reaction mixture were added hydrochloric acid (189 mg, 157 tl, 1.91 mmol, Eq:0.70) and sodium chloride (1.36 g, 1.36 ml, 23.3 mmol, Eq: 8.50). The mixture was stuffed for 15 mm, then poured into AcOEt (25 ml) and extracted. The aqueous layer was back- extracted with AcOEt (3 x 20 ml). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 0% to 90% EtOAc in heptane) to yield the title compound as white foam (560 mg;52 %). mlz = 393.0 [M+Hf?.

Statistics shows that 1-Amino-1-cyclopropanecarbonitrile hydrochloride is playing an increasingly important role. we look forward to future research findings about 127946-77-4.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ANSELM, Lilli; BANNER, David; HAAP, Wolfgang; KUHN, Bernd; LUEBBERS, Thomas; PETERS, Jens-Uwe; SPINNLER, Beat; WO2014/29722; (2014); A1;,
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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 939-80-0 as follows. 939-80-0

In a reactor, compound 2 (917 mg, 2.0 mmol), compound 4 (274 mg, 3.0 mmol) and Cs2CO3 (325 mg, 1.0 mmol) were added to dry THF (20 mL). Then the reactor was sealed under nitrogen, and the mixture was kept at 30 C., stirred for 12 hours. After the reaction, the mixture was diluted with dichloromethane (10 mL) and then filtered. The resulting filtrate was washed twice with water (2¡Á10 mL), and aqueous phases were combined, then the combined aqueous phases were extracted twice with dichloromethane (2¡Á10 mL). The organic layers were combined, dried over Na2SO4, and concentrated to obtain compound XVII as a light yellow powder (1004 mg, yield 90.2%), HPLC purity: 99.2%.

According to the analysis of related databases, 939-80-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; XU, YONG; (10 pag.)US2016/257667; (2016); A1;,
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