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. 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H3BrClN

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 was allowed to warm up to room temperature and stuffed for 2 hours. Ti(Oi-Pr)4 (13 g, 46 mmol) 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 pH10 with aq. NaOH solution, and exacted with EtOAc (3 x). 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+H]

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; 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; WO2014/191338; (2014); 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. 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

Into a boiling solution of 0.2 g of lithium in 50 mL of anhydrous 1-hexanol was added 1.0 g (2.6 mmol) of compound 3, 0.70 g (2.6 mmol) of compound 4, the mixture was maintained for 4 h, 1.4 g (2.0 mmol) of complex 1 was added, and the mixture was maintained for 2 h more. The solvent was distilled off, the reaction mass was dispersed in 50 mL of 10percent solution of acetic cid in acetone, the precipitate was filtered off, washed with 20 mL of 10percent ammonia solution, 100 mL of acetonitrile, 50 mL of water, and dried. Complexes 5?7 were treated with dichloromethane in a Soxhlet extractor, the extract was chromatographed on a column packed with silica gel Kieselgel 60 (Merck) (eluent dichloromethane?THF, 50 : 1 v/v). There with the mixture divided in three zones containing complexes 5?7 respectively. The complexes are dark-green powders well soluble in toluene, chloroform, dichloromethane, sparingly soluble in acetone, DMF.

According to the analysis of related databases, 1953-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Galanin; Shaposhnikov; Russian Journal of Organic Chemistry; vol. 51; 5; (2015); p. 727 – 732; Zh. Org. Khim.; vol. 51; 5; (2015); p. 727 – 732,6;,
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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. 101184-73-0, name is 2-(4-Bromophenyl)-2-methylpropanenitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 101184-73-0

To degassed toluene (200 mL) was added palladium acetate (0.30 g, 1.3 mmol) and x-phos (1.3 g, 2.7 mmol) and the mixture degassed a further 5 minutes. To the reaction mixture was then added cesium carbonate (35.0 g, 107 mmol), beta alanine ethyl ester hydrochloride (6.2 g, 40.4 mmol) and 2-(4-bromophenyl)-2-methylpropanenitrile (6.0 g, 26.8 mmol). The reaction mixture was heated at reflux for 2 hours, cooled and filtered through celite. Filtrate concentrated and the residue further purified on silica eluding with 25% ethyl acetate in heptane to give ethyl 3-(4-(2-cyanopropan-2-yl)phenylamino)propanoate (4.05 g, 58%) as a yellow solid. 1H NMR (300 MHz, CDCl3): delta ppm 1.26 (t, 3H), 1.66 (s, 6H), 2.60 (t, 2H), 3.44 (t, 2H), 4.15 (q, 2H), 4.18 (br s, 1H), 6.61 (d, 2H), 7.26 (d, 2H).

The synthetic route of 101184-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; pfizer Inc; US2010/197591; (2010); 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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 179897-89-3

To a solution of zinc chloride (50 mL, 1. OM in diethyl ether, 50 mmol) was added neopentylmagnesium chloride (50 mL, 1. OM in THF, 50 mmol) dropwise at 0 C. During the addition, the generated magnesium salts formed a white precipitate. The reaction was removed from the ice bath and allowed to stir for 1h, then 1- bromo-2-fluorobenzonitrile (5 g, 25 mmol) was added followed by bis (tri-tert- butylphosphine) palladium (0.127 g, 0.25 mmol, 1%). The reaction began to reflux and was placed back into the ice bath. After 1 h, the reaction was diluted with 200 mL of diethyl ether and washed with 1N HCI (2 x 100 mL), brine (100 mL), dried over magnesium sulfate and concentrated to give an oily solid (4.3 g, 22 mmol, 90%). H NMR (400 MHz, CDC13) 8 7.38-7. 30 (m, 2H), 7.11 (dt, J=8.5, 1.4 Hz, 1 H), 2.49 (s, 2H), 0.90 (s, 9H).

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 179897-89-3.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87751; (2005); A2;,
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Electric Literature of 179897-89-3, A common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-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 zinc chloride (50 mL, 1.0 M in diethyl ether, 50 mmol) was added neopentylmagnesium chloride (50 mL, 1.0 M in THF, 50 mmol) dropwise at 0 C. During the addition, the generated magnesium salts formed a white precipitate. The reaction was removed from the ice bath and allowed to stir for 1 h then 1-bromo-2-fluorobenzonitrile (5 g, 25 mmol) was added followed by bis (tri-tert- butylphosphine) palladium (0.127 g, 0.25 mmol, 1%). The reaction began to reflux and was placed back into the ice bath. After 1 h, the reaction was diluted with 200 mL of diethyl ether and washed with 1 N HCI (2 x 100 mL), brine (100 mL), dried over magnesium sulfate and concentrated to give an oily solid (4.3 g, 22 mmol, 90%).

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; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); A1;,
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Related Products of 97165-77-0,Some common heterocyclic compound, 97165-77-0, name is 3,5-Dibromobenzonitrile, molecular formula is C7H3Br2N, 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 79 3-(2′-amino-1^2,2-trimethyl-5′-oxo-r,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)-5- bromobenzonitrileA resealable glass pressure tube was charged with 2′-amino-l’,2,2-trimethyl-6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)spiro[chroman-4,4′-imidazol]-5′(rH)-one (50 mg, 0.13 mmol), 3,5-dibromobenzonitrile (34 mg, 0.13 mmol), dichloro[l, -bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (5.3 mg, 0.0065 mmol), 20% aqueous Na2C03 (241 mu., 0.45 mmol), and 1 ,4-dioxane (1.3 mL, 0.13 mmol). The reaction mixture was sparged with N? for 5 minutes, capped, stirred at 90C for 2 hours and allowed to cool to room temperature. The mixture was then diluted with EtOAc ( 10 mL) and washed with water (2 mL). The organic layer was separated, dried (MgS04), filtered and concentrated in vacuo. The residue obtained was purified by flash chromatography on silica gel (Biotage Flash 40S+) eluting with 5% MeOH/DCM. The product isolated was triturated with EtOAc. The solid formed was filtered, washed with additional EtOAc (2 X 1 mL) to provide 3-(2′-amino-r,2,2-trimethyI-5′-oxo- ,5′- dihydrospiro[chroman-4,4′-imidazole]-6-yl)-5-bromobenzonitrile ( 12 mg, 21% yield) as a solid. ‘H NMR (400 MHz, (CD3)2SO) delta 8.05 (s, 1H), 7.97 (s, 2H), 7.54 (d, J=7.04Hsz, 1H), 6.99 (s, 1 H), 6.88 (d,J=8.61Hz, 1H), 6.52 (br s, 2H), 3.05 (s, 3H), 2.19 (d, J=14.08 Hz, 1H), 1.82 (d, J=14.08 Hz, 1H), 1.43 (s, 3H), 1.39 (s, 3); LCMS (APCI+) m/z 439, 442 (M+H)+.

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

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
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1223434-15-8, name is Methyl 4-bromo-2-cyanobenzoate, 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. COA of Formula: C9H6BrNO2

Methyl 4-bromo-2-cyanobenzoate (800.0 mg; 3.33 mmol; 1.00 eq.) was combined with titanium(IV) isopropoxide (1.10 mL; 3.67 mmol; 1.10 eq.) in dry diethyl ether (16 mL) under argon atmosphere and ethylmagnesium bromide (2.22 mL; 3 M solution in diethyl ether; 6.67 mmol; 2.00 eq.) was added at rt. After 2h stirring, the reaction was quenched with 1N HCI (2 mL) and extracted with DCM. The organic extract was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was recrystallized from a mixture of diethyl ether and n-heptane giving 5′-bromospiro[cyclopropane-1,3′-isoindoline]-1′-one (385.0 mg; 49 %).

The synthetic route of 1223434-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 288251-96-7, name is 2-Isobutyl-5-nitrobenzonitrile, 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 288251-96-7, name: 2-Isobutyl-5-nitrobenzonitrile

To a solution of 2-isobutyl-5-nitrobenzonitrile (D56) (7.5 g) in methanol (80 mL) and water (80 mL) was added ammonium formate (51.9 g) and zinc (26.9 g). The reaction mixture was stirred at 80 C for 4 h. After cooling the reaction, the solid was filtered, the filtrate was concentrated under reduced pressure, the residue was extracted with EtOAc(300mL*2), the combined organic layers were washed with water (30mL*2), dried and concentrated to give 5-amino-2-(2- methylpropyl)benzonitrile (D57) (17.5 g) as a colorless solid. MS (ES): CnH14N2 requires 174; found 175.1 (M+H+).

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; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; REN, Feng; ZHAO, Baowei; WO2011/134280; (2011); A1;,
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Synthetic Route of 1250444-23-5,Some common heterocyclic compound, 1250444-23-5, name is 3-Bromo-2,6-difluorobenzonitrile, molecular formula is C7H2BrF2N, 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- bromo-2,6-difluorobenzonitrile (4.4 g, 20 mmol), potassium ethanethioate (2.88 g, 25 mmol), Pd2(dba)3 (0.555 g, 0.61 mmol) and Xantphos (0.70 g, 1.2 mmol) in p-dioxane (30 mL) was stirred at 102 C for 15 hours. After cooling to ambient temperature, 28% aqueous ammonium hydroxide (12.3 g, 202 mmol) was added. The mixture was stirred at ambient temperature for 1 hour. Water (50 mL) and 2: 1 MTBE/hexanes (200 mL) were added. The aqueous layer was separated, acidified with 1 N HC1 to pH~5 and extracted with MTBE (50 mL). The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 3: 1 hexane/CH2Cl2 to give 2,6-difluorG-3-mercaptobenzonitrie (0.74 g, 21 %) as solid.

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

Reference:
Patent; PELOTON THERAPEUTICS, INC.; DIXON, Darryl, David; GRINA, Jonas; JOSEY, John, A.; RIZZI, James, P.; SCHLACHTER, Stephen, T.; WALLACE, Eli, M.; WANG, Bin; WEHN, Paul; XU, Rui; YANG, Hanbiao; WO2015/35223; (2015); A1;,
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Synthetic Route of 85068-32-2,Some common heterocyclic compound, 85068-32-2, name is 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, molecular formula is C10H5F6N, 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.

An ethanol (10 mL) solution of 3,5-bis(trifluoromethyl)phenylacetonitrile (3.59 g, 14.2 mmol) and 2-ethylsulfanylaniline (2.54 g, 14.2 mmol) was cooled on ice, and an ethanol (10 mL) solution of sodium methoxide (1.2 g, 21.3 mmol) was sequentially added dropwise, followed by stirring under ice cooling for 72 hours. Water was poured in the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered to remove the white precipitate, and concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1:6) to afford the title compound (yielded 5.3 g, yield: 87%) as a red-tan oily product. 1HNMR Spectrum (CDCl3) sigma: 8.29 (2H, s), 7.79 (1H, s), 7.58-7.52 (2H, m), 7.44-7.39 (2H, m), 4.00 (2H, br), 2.87 (2H, q, J=7.3 Hz), 1.27 (3H, t, J=7.3 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-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, its application will become more common.

Reference:
Patent; HOKKO CHEMICAL INDUSTRY CO., LTD.; HIROKI, Hidekatsu; KOBAYASHI, Yuta; SUZUKI, Jun; ONOUE, Shinji; IWASAKI, Katsuhiko; OOTAKA, Akihito; DOI, Hayato; MATSUO, Eiko; ONOUE, Miwa; OKIMOTO, Asako; (68 pag.)US2018/290986; (2018); A1;,
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