Tag: M.W=200-300

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. 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile, A new synthetic method of this compound is introduced below., name: 4-Bromo-2-methoxybenzonitrile

To a mixture of 4-bromo-2-methoxy benzonitrile (1 g, 4.72 mmol), butyl vinyl ether (2.362 g, 23.58 mmol), l,3-bis(diphenylphosphino)propane (0.097 g, 0.236 mmol), palladium (II) acetate (0.053 g, 0.236 mmol) and l-butyl-3-methylimidazolium tetrafluoro borate (0.533 g, 2.358 mmol) in DLC/MSO (4.72 ml) was added diisopropylamine (0.807 ml, 5.66 mmol) in a microwave vial. The reaction mixture was degassed with argon and stirred at 115°C for 18h. The mixture was partitioned between EtOAc and H20 and the aqueous layer was extracted with EtOAc (3x). The combined organic phase was washed with brine, dried over anhydrous MgS04, and filtered. The residue was then dissolved in MeOH/DLC/MSO (25ml/5ml), then 3N HC1 (20 ml) was added. The mixture was stirred at rt for 3h. After concentration the residue was partitioned between DCM and water and the aqueous layer was extracted with DCM (3x). The combined organic phase was washed with brine, dried over anhydrous MgS04, and filtered. The filtrate was concentrated and purified by silica gel column chromatography using (0-60)percentEtOAc/Hexanes as mobile phase to give the title product as a pale yellow solid.

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; MERCK SHARP & DOHME CORP.; CHOBANIAN, Harry; PIO, Barbara; GUO, Yan; DING, Fa-Xiang; DONG, Shuzhi; WALSH, Shawn, P.; JIANG, Jinlong; KIM, Dooseop; WO2015/95097; (2015); A2;,
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1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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. Product Details of 1953-99-7

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-phenylphenol (3.21 g), K2CO3 (3.9 g) and acetone (25 ml) were placed in a 100 ml flask and stirred while heating to 70 ° C. After completion of the reaction, the solid matter is obtained by filtering and distilling off the liquid obtained by washing with acetone. At this time, the obtained solid is dissolved in a small amount of dichloromethane, washed with nucleic acid several times, filtered and vacuum dried to obtain 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Seo Hye-won; Shin Myeong-yeop; Jeong Ui-su; Han Gyu-seok; (56 pag.)KR2019/11995; (2019); A;,
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1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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. name: 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile

As it is shown in Scheme 3 above, 3,4,5,6-tetra-chloride in a nitrogen gas rope phthaloyl nitrile (tetrachlorophthalonitrile) (5.0mmol), 2,5- di (di) – [tert (tert) – butyl (butyl ) -4-methoxyphenol (methoxyphenol) (1.5 eq.), potassium carbonate (K 2 CO 3) (10 equivalents) of anhydrous (anhydrous) dissolved in 30ml DMF after 12 hours at 80 dongan reflux (reflux) thereby.After completion of reaction, the reaction solution into ice water slowly degrades (ice water) (dropwise). Then, methylene chloride: then extracted three times, magnesium sulfate (MgSO with (methylene chloride MC) 4 is removed by passing the water in) and evaporated (evaporation).Then, the obtained phthalonitrile (phthalonitrile) precursor to the dried crude product (crude product) was purified by column chromatography (column chromatography).

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Display Co., Ltd; Seoul National University Industry-Academic Cooperation Foundation; Kim, Young Hun; Ahn, Byung Gun; Han, Sang Hun; Kim, Jae Pil; Choe, Jun; Namgung, Jinung; (13 pag.)KR2016/5258; (2016); A;,
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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. 92616-49-4, name is 4-Bromo-1-naphthonitrile, A new synthetic method of this compound is introduced below., name: 4-Bromo-1-naphthonitrile

Compound B (11.60 g, 50 mmol) was dissolved in dry THF (200 mL) and stirred, and LiAlH4 (2.77 g, 73 mmol) was added slowly in portions with cooling in an ice-water bath. After completion of the addition, the reaction mixture was stirred in the ice-water bath for another 2 hours. The reaction mixture was carefully and slowly poured into stirring ice water (400 mL), stirred, and extracted with CH2Cl2 (200 mL3). The extracted organic phases were combined, washed with 5% saline solution (200 mL), and dried over anhydrous Na2SO4. The dried organic phase was evaporated on a rotary evaporator to remove the solvent, and the resulting residue was purified by column chromatography to give product C as a colorless oil. 1H NMR showed that about 30% debromination by-product (i.e., naphthalene-1-methylamine) was contained therein and a further purification was difficult, and therefore the mixture was used for the next reaction directly.

The synthetic route of 92616-49-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIANJIN INSTITUTE OF PHARMACEUTICAL RESEARCH CO., LTD.; Zhao, Guilong; Liu, Changying; Liu, Yuqiang; Chen, Huihui; Li, Yuquan; Zhang, Haizhi; Xie, Yafei; Wu, Jingwei; Liu, Wei; Xu, Weiren; Zou, Meixiang; Tang, Lida; US2019/233381; (2019); 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, Application In Synthesis of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile

6-Bromo-3-amino-4,5,7-1H-indazole; A solution of 5 g of 4-bromo-2,3,5,6-tetrafluorobenzonitrile in 90 mL of ethanol is admixed with 9.7 mL of hydrazine hydrate. The reaction mixture is stirred for 17 hours at reflux and then concentrated under reduced pressure. The residue obtained is stirred for 30 minutes in 80 mL of distilled water. The suspended solid is isolated by filtration, washed with water, treated with suction and then triturated in 200 mL of ethyl ether and isolated by filtration, to give 1.03 g of 6-bromo-3-amino-4,5,7-1H-indazole, whose characteristics are as follows: MS spectrum (ES+): m/z=267 [MH+]

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; Aventis Pharma S.A.; US2007/161626; (2007); 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. 215800-25-2, name is 2-(4-Bromo-3-methylphenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(4-Bromo-3-methylphenyl)acetonitrile

A mixture of 2-(4-bromo-3 -methylphenyl)acetonitrile (1 .50 g, 7.14 mmol, 1.0 eq), (2-fluorophenyl)boronicacid (1.19 g, 8.56 mmol, 1.2 eq), CsF (2.38 g, 15.70 mmol, 2.2 eq), Pd(PPh3)4 (0.41 g, 0.35 mmol, 0.05 eq) in DMF (15 mL) was stirred at 90 C under nitrogen atmosphere for 18 h. After complete consumption of starting material, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate. The organic extract was separated and the aqueousextract was again extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous Na2SO4, filtered and solvents evaporated from the filtrate under reduced pressure to obtain a crude, which was purified by flash chromatography on silica gel, 23 0-400 mesh, using gradient of ethyl acetate in hexanes as eluent to obtain 2-(2?-fluoro-2- methyl-[1,1?-biphenyl]-4-yl)acetonitrile as yellow oil, yield (1.12 g, 70%).

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 215800-25-2.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; BARTA, Thomas, E.; BOURNE, Jonathna, William; MONROE, Kyle, D.; MUEHLEMANN, Michael, M.; PANDEY, Anjali; BOWERS, Simeon; (59 pag.)WO2017/34990; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-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 36282-26-5, HPLC of Formula: C7H3BrFN

To a solution of 2-bromo-4-fluorobenzonitrile (0.5 g, 2.50 mmol) and phenol (0.25 g, 2.62 mmol) in DMSO (2 mL), at RT, K2C03 (0.69 g, 5 mmol) was added and the reaction mixture was stirred at RT overnight. Water and Et20 were added to the reaction mixture, the organic phase was washed withwater and saturated NaHCO3, dried and the solvent removed under reduced pressure. Crude materialwas purified by FC on silica gel (eluent: Cy/EA from 100/0 to 90/10) to give 2-bromo-4-phenoxybenzonitrile (p21, 220 mg, y= 32%).1H NMR (CHLOROFORM-d): 6 ppm 7.60 (d, 1 H) 7.42 – 7.51 (m, 2 H) 7.26 – 7.33 (m, 1 H) 7.23 (d, 1 H)7.09 (d, 2 H) 6.98 (dd, 1 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, 2-Bromo-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHIRE INTERNATIONAL GMBH; CREMONESI, Susanna; LUKER, Tim; SEMERARO, Teresa; MICHELI, Fabrizio; (257 pag.)WO2016/42452; (2016); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 1953-99-7,Some common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

3,4,5,6-tetrachlorophthalonitrile of 6 g (3 eq), KF of 1.8 g (3.1 eq), CaCO3 of 0.5 g (0.5 eq) and 1,2 ethanol of 2.5 g (4 eq) are put in acetone of about 30 ml to about 50 ml (30 eq), and reaction proceeds at room temperature overnight. When the completion of the reaction is verified by thin later chromatography (TLC), work-up is carried out. Subsequently, a resultant product is separated and purified by column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, its application will become more common.

Reference:
Patent; Samsung Display Co., Ltd.; Kim, Hyunjin; Kang, Sunwoo; Lee, Daewon; Huh, Chul; (14 pag.)US2016/327709; (2016); A1;,
Nitrile – Wikipedia,
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Reference of 179898-34-1, A common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 solution of 2-(pyridin-2-yl)-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridine (20 mg, 0.1 mmol) in toluene was added 3-bromo-5-fluorobenzonitrile (30 mg, 0.15 mmol), Cs2CO3 (65 mg, 0.2 mmol), Pd(OAc)2 (1 mg, cat.), and Xantphos (2 mg, cat.). The mixture was heated to 1000C and stirred overnight. The mixture was cooled, dissolved in MeOH, and filtered. The filtrate was concentrated and the residue was purified by preparative TLC to afford 3-fluoro-5-(2-(pyridin-2-yl)-6,7-dihydrooxazolo- [5,4-c]pyridin-5(4H)-yl)benzonitrile (10 mg, 31%) as a yellow solid. 1H NMR (400 MHz, CDCl3): delta 8.68 (d, IH); 8.05 (d, IH), 7.77 (t, IH), 7.32 (t, IH), 6.90 (s, IH), 6.75 (m, 2H), 4.40 (s, 2H), 3.68 (t, 2H), 2.80 (t, 2H); LC/MS: m/e = 321 (M+H)+.

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

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
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Some common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, molecular formula is C9H6BrNO, 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: C9H6BrNO

General procedure: Method C: Almac CRED (200 mg) andNADP or NAD (10 mg) were measured into a 250 mL roundbottomedflask then dissolved in 0.1 M potassium phosphate buffer(pH 7, ca. 50 mL). IPA (7 mL) was added, followed by a solutionof ketone (900-1700 mg) in DMSO (2.5-5 mL, depending on solubility).This was stirred at 35 C under 500 mbar reduced pressureto aid removal of acetone formed by IPA oxidation. Standardwork-up procedure: The pH of the reaction mixture was adjustedif necessary (basic or acidic depending on estimated pKa of alcoholproduct) with either 1 M NaOH or 1 M HCl. The reaction mixturewas then extracted with MTBE (3 100 mL).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4592-94-3, its application will become more common.

Reference:
Article; Rowan, Andrew S.; Moody, Thomas S.; Howard, Roger M.; Underwood, Toby J.; Miskelly, Iain R.; He, Yanan; Wang, Bo; Tetrahedron Asymmetry; vol. 24; 21-22; (2013); p. 1369 – 1381;,
Nitrile – Wikipedia,
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