Tag: M.W=100-200

Synthetic Route of 194853-86-6, 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. 194853-86-6 name is 4-Fluoro-2-(trifluoromethyl)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.

COMPARATIVE EXAMPLE A This example illustrates the preparation of 4-[(1S, 4S)-4-Hydroxy-1- 0 methylpentyloxy]-2-trifluoromethylbenzonitrile, using a strong base under anhydrous conditions, as described in co-pending United States patent application serial number 11/053,010.A 10 L, jacketed ChemGlass reactor was fitted with a mechanical stirrer, nitrogen sweep line, and NesLab chiller. The vessel was purged with nitrogen for 5 15 minutes and then charged with 61 g (1.5 mol) of sodium hydride (60% in mineral oil) and 2.0 L of tetrahydrofuran (1THF”). The suspension was stirred and cooled to 6.5C and then a solution of 180.3 g (1.53 mol) of (2S,5S)-(+)-2,5- hexanediol in 1.0 L of THF was added, in 4 portions, over 35 minutes. The mixture became very thick and 1.0 L of THF was added about halfway through Q the addition in order to facilitate better stirring. The maximum internal temperature observed was 14.4C. The suspension was stirred for 30 minutes and then 288.1 g (1 .52 mol) of 4-fluoro-2-(trifluoromethyl)benzonitrile was added. The mixture was further diluted with another 1.0 L of THF and then warmed to room temperature and allowed to stir overnight (a clear solution was obtained after 30 minutes). HPLC analysis at the 21 hour point showed a 48:45 mixture of the expected product (3) to the bis-alkylated byproduct (4). Water (3.0 L) and ethyl acetate (4.0 L) were added and the layers separated. The organic layer was washed with 2 x 2.0 L of water and 1 x 2.0 L of brine. The aqueous layers were back-extracted with 2.0 L of ethyl acetate and then the organic layers were combined and evaporated at the Rotavap. The residue was twice dissolved in 1.0 L of 2-propanol and evaporated at the Rotavap (to remove water). The crude product was twice purified by flash chromatography on silica gel using dichloromethane/methanol. A third chromatography column (Biotage system) was carried out using ethyl acetate/hexanes. The purified target was isolated as 149.8 g (34%) of an oil. The material assayed at >99% purity (a/a, HPLC) and had a proton NMR spectrum consistent with structure.

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

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/136910; (2006); A1;,
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5414-21-1, name is 5-Bromovaleronitrile, 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. Formula: C5H8BrN

In a four-neck reactor equipped with a thermometer, in a nitrogen stream, 2-hydrazinobenzothiazole 10.0 g (60.5 mmol) of DMF were dissolved in 100 ml of DMF . To this solution, 41.8 g (304 mmol) of potassium carbonate, And 10.34 g of 5-bromovaleronitrile ( 60.6 mmol), and the whole was stirred at 60 C. for 8 hours. After completion of the reaction, The reaction solution was added to 20 C., and the mixture was poured into 1,000 ml of water, And extracted with 1000 ml of ethyl acetate. After drying the ethyl acetate layer with anhydrous sodium sulfate, Sodium sulfate was filtered off. Ethyl acetate was distilled off from the filtrate under reduced pressure by a rotary evaporator, A yellow solid was obtained. This yellow solid was dissolved in Siri Kagel column chromatography (N-hexane: ethyl acetate = 60: 40) To obtain 6.82 g of Intermediate T as a white solid (yield: 45.7%).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZEON CORPORATION; SAKAMOTO, KEI; OKUYAMA, KUMI; SANUKI, KANAKO; (78 pag.)JP6090514; (2017); B1;,
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Synthetic Route of 90381-43-4,Some common heterocyclic compound, 90381-43-4, name is 7-Methoxy-2-naphthonitrile, molecular formula is C12H9NO, 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 solution of 7-methoxy-2-naphthonitrile (501 mg, 2.74 mmol) and KOH (503 mg, 9.0 mmol) in 95% ethanol (5 mL) is heated to reflux for 24 hours. The reaction mixture is allowed to cool, diluted with water and then acidified to pH<2 with concentrated HCl. The resulting precipitate is collected by filtration, washed with water and dried by heating at 70 C. under vacuum to give 7-methoxy-2-naphthoic acid as a white solid (540 mg, 98%). HRMS (FAB) calculated for C12H10O3+H+: 203.0708, found 203.0701. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Methoxy-2-naphthonitrile, its application will become more common. Reference:
Patent; Jacobsen, Eric Jon; Myers, Jason K.; Walker, Daniel Patrick; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Acker, Brad A.; Groppi JR., Vincent E.; US2003/236270; (2003); A1;,
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Synthetic Route of 915394-28-4, A common heterocyclic compound, 915394-28-4, name is 2-Methyl-2-(3-nitrophenyl)propanenitrile, molecular formula is C10H10N2O2, 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-Methyl-2-(3-nitrophenyl)propanenitrile (0.6 g, 3.15 mmol) obtained in Step (1) above was stirred in a solvent of methanol. The reaction solution was mixed with Pd/C (0.06 g, 0.56 mmol), followed by stirring under hydrogen conditions for about 2 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (0.48 g, 95 %). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 7.06 (t, 1H), 6.71 (s, 1H), 6.61 (d, 1H), 6.52 (d, 1H), 5.21 (s, 2H), 1.61 (s, 6H). MS (ESI+, m/z): 161 [M+H]+

The synthetic route of 915394-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hanmi Pharm. Co., Ltd.; BAE, In Hwan; HAN, Sang Mi; KWAK, Eun Joo; AHN, Young Gil; SUH, Kwee Hyun; EP2876107; (2015); A1;,
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Synthetic Route of 654-70-6, A common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

4-Isothiocyanato-2-trifluoromethylbenzonitrile (96); 4-Amino-2-trifluoromethylbenzonitrile (2.23 g, 12 mmol) was added portionwise over 15 min into a well-stirred heterogeneous mixture of thiophosgene (1 mL, 13 mmol) in water (22 mL) at room temperature. Stirring was continued for an additional 1 h. The reaction medium was extracted with chloroform (3¡Á15 mL). The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure to yield desired product 4-Isothiocyanato-2-trifluoromethylbenzonitrile (96) (2.72 g, 11.9 mmol, 99%) as brownish solid and was used without further purification.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of California; US2009/111864; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, 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 67832-11-5, Recommanded Product: 67832-11-5

Methyl magnesium bromide (3 M in tetrahydrofuran) was added at rt drop wise to a solution of 4-bromo-2-methylbenzonitrile (4 g) in dry THF (15 mL) and was then heated to reflux for 2 h and then stirred at rt for 3 d. The mixture was chilled in an ice bath, saturated aqueous ammonium chloride solution (100 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were concentrated under reduced pressure and the remaining residue was treated with 4 N HCl at 0 C. and was stirred at rt for 18 h. The mixture was extracted with EtOAc and the organic layer was washed with water, dried and the solvent was removed under reduced pressure to yield the desired product (88% yield).

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; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194443; (2014); A1;,
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Application of 1187-42-4, These common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, 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.

The compound D (0.70 g, 1.50 mmol), diaminomaleonitrile (0.19 g, 1.80 mmol), 40 mL of ethanol, 40 mL of THF (tetrahydrofuran), and 0.23 mL of 12M hydrochloric acid were charged in a three-necked flask having a capacity of 300 mL, and then the resultant mixture was stirred while conducting heating at 40 C. for 24 hours. Water was added to the resultant solution, the resultant mixture was subjected to extraction with chloroform, and then the resultant extract was dried by adding sodium sulfate thereto. Sodium sulfate hydrate was removed by filtration, and the solvent was distilled off from the filtrate using an evaporator. The resulting solid was purified by silica gel column chromatography (developing solvent: toluene) to obtain a red solid (yield amount: 0.40 g, yield: 49%). Chemical shift values (delta) of the compound measured by 1H NMR (400 MHz, CDCl3) were as follows: delta 9.31 (d, J=8.8 Hz, 1H), 9.24 (dd, J=8.0 Hz, 1.2 Hz, 1H), 8.90 (d, 1.6 Hz, 1H), 8.78 (d, J=8.4 Hz, 1H), 8.13 (dd, J=8.4 Hz, 1.6 Hz, 1H), 8.05 (d, J=8.4 Hz, 2H), 8.00 (td, J=7.2 Hz, 1.6 Hz, 1H), 7.89 (td, J=7.2 Hz, 1.2 Hz 1H), 7.57 (d, J=8.4 Hz, 2H), 6.69 (m, 6H), 6.06 (dd, J=8.0 Hz 2.0 Hz, 2H). It was confirmed by 1H NMR measurement that the obtained compound was a compound 1 (Px-CNBQx).

The synthetic route of 1187-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION; Nippon Soda Co., Ltd.; YASUDA, Takuma; FURUE, Ryuhei; ISHIHARA, Hiroyuki; FUKUSHIMA, Yukio; (61 pag.)US2019/330162; (2019); 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 4640-66-8 as follows. Product Details of 4640-66-8

General procedure: To a 0.5-2.0ml vial with 1 mmol ketone (1 eq) issolved in 2-pentanol (1.66 M) was added 1.1 eq of aromatic aldehyde and catalytic piperidine (0.08 eq), stirring vigorously. After heating under muWave for 15min at 120 C, the reaction was cooled to r.t. and precipitate was vacuum filtered and washed with minimal, cold hexanes. After drying under vacuum, solid was analyzed via NMR, IR, and mp.

According to the analysis of related databases, 4640-66-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Deshpande, Shyam J.; Leger, Paul R.; Sieck, Stephen R.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1772 – 1775;,
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Some common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, 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. Formula: C12H11NO

A solution of 2,2-dimethyl-2H-chromene-6-carbonitrile (300 mg, 1.62 mmol) in diethyl ether (2 ml) was added dropwise to a suspension of lithium aluminum hydride (135 mg, 3.56 mmol) in diethyl ether (3 ml) at 0 C. After 30 minutes of stirring at 0 C the mixture was brought to room temperature. After 1 hour of stirring at room temperature, sodium sulfate decahydrate was added in small portions until gas evolution ceased. The mixture was filtered and the organic solution was concentrated to oil (269 mg, 88 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33143-29-2, its application will become more common.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; OLSSON, Roger; BORGSTROeM, Bjoern, Gustav; JANSSON, Karl, Erik; SKOeLD, Niklas, Patrik; VON WACHENFELDT, Henrik; WAHLSTROeM, Larisa, Yudina; (250 pag.)WO2019/40107; (2019); A1;,
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Synthetic Route of 42872-73-1, These common heterocyclic compound, 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, 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.

[0803] 0.545 g (2.70 mmol) of 2-bromo-4-methylbenzo- nitrile, 1.87 g (2.70 mmol, 61% purity, 1 eq.) of tert-butyl 4-methoxy-2-[5-methoxy-2-oxo-4-(4,4,5,5-tetramethyl- 1,3, 2-dioxaborolan-2-yl)pyridin-1 (2H)-yl]butanoate (racemate) and 1.12 g (8.08 mmol, 3 eq.) of potassium carbonate were initially charged in 27 ml of dioxane under argon, 66 mg (0.08 mmol, 0.03 eq) of [1,1 -bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex were added, and the mixture was stirred at 80 C. for 16 h. The reaction mixture was cooled and filtered through kieselguhr, and the filtercake was washed with dichloromethane and acetonitrile. The filtrate was concentrated and the residue was then purified by means of normal phase flash chromatography (eluent: cyclohexane/ethyl acetate, 0-70%). Yield:1.04 g (85% purity, 80% of theory).10804] LC/MS [Method 10]: R=1.86 mm; MS (ESIpos):mlz=413 (M+H), 10805] ?H-NMR (400 MHz, DMSO-d5): oe [ppm]=7.80 (d, 1H), 7.43 (d, 1H), 7.39 (s, 1H), 7.34 (s, 1H), 6.38 (s, 1H),5.15-5.05 (m, 1H), 3.62 (s, 3H), 3.43-3.35 (m, 1H), 3.23-3.11 (m, 4H), 2.42 (s, 3H), 2.38-2.29 (m, 2H), 1.40 (s, 9H).

Statistics shows that 2-Bromo-4-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 42872-73-1.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ-NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; ACKERSTAFF, Jens; STAMPFUss, Jan; (87 pag.)US2017/291892; (2017); A1;,
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