Category: nitriles-buliding-blocks

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. 57381-39-2, name is 2-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Bromo-5-fluorobenzonitrile

A suspension of [2-BROMO-5-FLUOROBENZONITRILE] (30.0 g, 150 mmol), bis (pinacolato) diboron (41.9 g, 165 mmol) and potassium acetate (29.4 g, 300 mmol) in 1,4-dioxane (375 ml) and DMSO (30 ml) was degassed with nitrogen for 1 h. Dichloro [[L,] [1′-BIS] (diphenylphosphino) ferrocene]- palladium (II) dichloromethane adduct (3.7 g, 4.5 mmol) was added and the mixture heated at [90C] for [18] h. The mixture was allowed to cool to ambient temperature then diluted with diethyl ether (300 ml) and filtered through a glass microfibre filter paper. The solvent was evaporated and the residue was treated with ice-cold 2N sodium hydroxide solution (250 ml) and the mixture left to stir for 15 min. The aqueous phase was extracted with diethyl ether (200 ml). The pH of the aqueous was adjusted to 5 by the addition of concentrated hydrochloric acid. The aqueous phase was extracted with diethyl ether (2 x 200 ml), the organic phase was combined, washed with water (150 ml) and brine (150 ml), dried over anhydrous sodium sulphate, filtered and evaporated to give 5-fluoro-2- (4,4, 5, [5-TETRAMETHYL- [1,] 3,2] dioxaborolan-2-yl) benzonitrile (36.5 g, [98%)] as a brown oil which crystallised on standing: [5H] (360 MHz, CDCl3) 1.38 (12H, s), 7.25-7.30 (1H, m), 7.40 (1H, dd, J 3 and 8), 7.91 (1H, dd, J 6 and 8). 5-Fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)- benzonitrile (0.99 g, 4.0 mmol) and [1,] 3-dibromo-5-fluorobenzene (1.52 g, [6.] 0 mmol) were suspended in 1,2-dimethoxyethane (8 ml) and 2N sodium carbonate solution (4 [ML)] and degassed for 30 min before addition of tetrakis (triphenylphosphine) palladium [(0).] On complete addition the mixture was heated at [65C] for 20 h. The mixture was partitioned between ethyl acetate (100 ml) and water (50 ml), the organic layer separated and washed with brine (50 ml), dried over anhydrous sodium sulphate, filtered and evaporated onto silica. The product was purified by flash column chromatography on silica, eluting with isohexane on a gradient of diethyl ether (5-100%). Combination of the desired fractions and evaporation gave [3′-BROMO-4,] [5′-DIFLUOROBIPHENYL-2-CARBONITRILE] (110 mg, 9%) as a white solid: [SN] (500 MHz, [CD13)] 7.53-7. 55 [(1H,] m), 7.67 (1H, s), 7.69-7. 76 (3H, m), 8.03 [(1H,] dd, [J 9 AND] 2). [2- (8-FLUOROIMIDAZO [L,] 2-a] [PYRIDIN-7-YL)] propan-2-ol (58 mg, 0.3 mmol) and 3′-bromo-4, [5′-DIFLUOROBIPHENYL-2-CARBONITRILE] (106 mg, 0.36 mmol) were coupled following the procedure in Example 6 to afford 4,3′-difluoro- 5′- [8-fluoro-7- (l-hydroxy-l-methylethyl) imidazo [1, [2-A] PYRIDIN-3-YL]-] [BIPHENYL-2-CARBONITRILE] (25 mg, 20%) as a white solid: [SN] (500 MHz, [CD13)] 1.74 (6H, s), 2.07 [(1H,] s), 7.22-7. 26 (2H, m), 7.35 [(1H,] d, J 9), 7.39-7. 45 [(1H,] m), 7.51-7. 57 (3H, m), 7.76 [(1H,] s), 8.35 [(1H,] d, J 7) ; [RNLZ] (ES+) 408 (100%, [[MH] +).]

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 57381-39-2.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/99816; (2003); A1;,
Nitrile – Wikipedia,
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Application of 64113-85-5, 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 64113-85-5 as follows.

2-cyanobiphenyl-4-carboxylic acid, 11 The compound 9 (1.1 g, 6.0 mmol) is dissolved in pyridine (10 mL) and water (2 mL). To this solid, KMnO4 (0.9 g, 6.0 mmol, 1 equiv.) is added, and the reaction is heated to reflux. Additional 0.25 equiv. of KMnO4 is added every 30 min. for 1O h. The reaction is further refluxed for 50 h and filtered hot and the filtrate is evaporated under reduced pressure. The residue is dissolved in 20 mL water with heating. The solution is acidified to pH 2 with cone. HCl after cooling to room temperature. The white precipitate is collected by filtration and washed generously with cold water and the product is dried under vacuum overnight. Yield 1.1 g, 86 %; mp 195-200 0C; 1HNMR (400 MHz, CDCl3) delta 2; 13CNMR (101 MHz, CDCl3) delta 2; IR (Neat, cm’1); GC-MS (EI) m/z (M+); Anal. (Ci4Hi ^0.0.75H2O) C, H, N.

According to the analysis of related databases, 64113-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GOVERNMENT OF THE UNITED STATES OF AMERICA, REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; WO2008/92072; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 25978-68-1, 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. 25978-68-1, name is Methyl 4-cyano-3-methylbenzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 4-cyano-3-methyl-benzoic acid methyl es­terfrom Example E2h.l (1.6g, 9.3mmol) in methanol (50ml) to 0C was treated with cobalt(II) chloride hexahydrate (5.1g, 18.6mmol). The mixture was stirred for 15min at room temperature then sodium borohydride (3.5g, 93mmol) was added portionwise. The reaction mixture was stirred for 90min then concentrated NH3 (5ml) was added drop-wise. The mixture was warmed up to room temperature over 30min, filtered through Celite filter agent, washed with methanol and the filtrate was concentrated in vacuo. The residue was purified by flash chromatog­raphy on silica gel (eluant; 1% 35% ammonia:10% metha­nol: 89% dichloromethane) to yield the title compound (670mg, 37%) .

The synthetic route of Methyl 4-cyano-3-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERRING B.V.; WO2006/21213; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1246213-27-3, name is 2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile, 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 1246213-27-3, name: 2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile

To a stirred solution of compound 7 (20 g, 0.065 mol) in toluene (300 mL), was added drop wise DIBAH (80 mL, 1 M in toluene) at about -60 to -50 0C. After stirring for 2 hours, 6 N HCl (300 mL) was added to the reaction mixture and stirring was continued for 30 minutes. The organic layer was then separated, washed with 2 N HCl followed by a NaHCtheta3 solution, then a brine solution, dried over Na2SO4 and concentrated in vacuo to afford the compound 8 as an oil. The product was used in the next reaction without further purification. 1H NMR (CDCl3; 400 MHz) delta 9.61 (s), delta 7.36 (m), delta 7.25 (m), delta 6.87 (m), delta 5.06 (m), delta 1.43 (S), delta 1.33 (s).

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Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DEMATTEI, John; LOOKER, Adam, R.; NEUBERT-LANGILLE, Bobbianna; TRUDEAU, Martin; ROEPER, Stefanie; RYAN, Michael, P.; YAP, Dahrika, Milfred Lao; KRUEGER, Brian, R.; GROOTENHUIS, Peter, D.J.; VAN GOOR, Frederick, F.; BOTFIELD, Martyn, C.; ZLOKARNIK, Gregor; WO2010/108162; (2010); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 38469-84-0,Some common heterocyclic compound, 38469-84-0, name is 5-Methoxy-2-nitrobenzonitrile, molecular formula is C8H6N2O3, 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-Amino-5-methoxybenzonitrile: [0441] A 100 mL round bottom flask was charged with 5-methoxy-2- nitrobenzonitrile (1.7 g, 9.55 mmol), sodium dithionite (4.99 g, 29 mmol), water (15 mL) and EtOH (50 mL). The resulting mixture was heated at reflux for 1 h. Work-up: the reaction mixture was concentrated in vacuo to remove ethanol then extracted with EtOAc (50 mL). The organic layer was dried over anhydrous Na2S04 and concentrated in vacuo, to afford 1.4 g (quantitative) of the product as yellow oil. It was used in the next step without further purification.

The synthetic route of 38469-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; BORCHARDT, Allen; DAVIS, Robert; BEAUREGARD, Clay; BECKER, Daniel; GAMACHE, Daniel; NOBLE, Stewart, A.; HELLBERG, Mark, R.; KLIMKO, Peter, G.; ZHIHAI, Qui; PAYNE, Joseph, E.; YANNI, John; WO2011/112731; (2011); A2;,
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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 138642-47-4 as follows. HPLC of Formula: C8H6BrNO

Step A: 1-(2-Bromo-5-methoxyphenyl)methanamine 2-Bromo-5-methoxybenzonitrile (10.0 g, 47.2 mmol) was dissolved in dry tetrahydrofuran (100 mL) in a flame-dried flask and cooled in an ice bath. A solution of borane in tetrahydrofuran (75 mL, 75 mmol, 1.0 M) was added dropwise over a period of 30 minutes. The reaction mixture was stirred overnight at rt, then quenched slowly with ice water and Na2CO3 (saturated aqueous solution). After removal of THF, the residue was extracted with large amounts of EtOAc three times. The combined organic layers were washed with water, dried, and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product as a white powder (3.65 g, 36%). LCMS for C8H10BrNO (M+H)+: m/z=216.9, 219.0.

According to the analysis of related databases, 138642-47-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; US2010/190804; (2010); A1;,
Nitrile – Wikipedia,
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Some common heterocyclic compound, 86770-80-1, name is 3,3-Difluorocyclobutanecarbonitrile, molecular formula is C5H5F2N, 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. Product Details of 86770-80-1

A solution of 3,3-difluorocyclobutane-l-carbonitrile (1 g, 8.54 mmol) in ethanol (15 mL) was treated with hydroxylamine (50% in water) (5.25 mL, 86.0 mmol) and stirred at 80 C for 3 h. The reaction mixture was allowed to cool and then concentrated in vacuo. The residue was partitioned between DCM (10 mL) and water (10 mL). The organic phase was separated, the aqueous phase was extracted with DCM (3 x 5 mL),. The product re-extracted with 1 : 1 IPA/CHCI3 (3 x 60 mL), organic separated and dried over sodium sulfate and concentrated in vacuo to afford the title compound as an orange gum (545 mg,42%). 1H NMR (500 MHz, DMSO-d6) delta 9.07 (s, 1H), 5.44 (s, 2H), 2.84 – 2.59 (m, 5H). LCMS (ES+) RT 0.25 min, 151.0 (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 86770-80-1, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki, Peter; BRACE, Gareth, Neil; BROWN, Julien, Alistair; CALMIANO, Mark, Daniel; CHOVATIA, Praful, Tulshi; DELIGNY, Michael; GALLIMORE, Ellen, Olivia; HEER, Jag, Paul; JACKSON, Victoria, Elizabeth; KROEPLIEN, Boris; MAC COSS, Malcolm; QUINCEY, Joanna, Rachel; SABNIS, Yogesh, Anil; SWINNEN, Dominique, Louis, Leon; ZHU, Zhaoning; WO2015/86526; (2015); A1;,
Nitrile – Wikipedia,
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Electric Literature of 17354-04-0, 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 17354-04-0 as follows.

General procedure: Piperidine (0.03 ml, 5 mol %) was added to a warm solution of the appropriate salicylaldehyde 5 (5 mmol) and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (1.12 g, 5 mmol) in EtOH (10 ml). The resulting solution was refluxed with stirring for 5 h. The mixture was treated with a solution of concentrated H2SO4 (0.55 ml) in EtOH (2 ml) and refluxed with stirring for 2 h. The obtained precipitate was filtered, washed with EtOH (10 ml), hot H2O (40 ml) and finally with EtOH (10 ml), and dried at 100 C.

According to the analysis of related databases, 17354-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
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Synthetic Route of 64113-86-6, A common heterocyclic compound, 64113-86-6, name is 5-Methyl-2-nitrobenzonitrile, molecular formula is C8H6N2O2, 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.

5-Methyl-2-nitrobenzonitrile (1.92 g, 11.84 mmol) was added in portions to a stirred solution of SnCl2 (11.22 g, 59.2 mmol) in conc. HCl (12 mL) and EtOH (12 mL). The reaction temperature was maintained at 20-30 C. using an ice bath. The reaction mixture was then stirred at room temperature for 1 h and poured into an ice cold aqueous solution of NaOH (6N, app. 30 mL) to neutralize to pH7. The product was extracted into EtOAc, washed with brine, dried over MgSO4 and concentrated to provide the title product (1.56 g, 99%) as a yellow-brown solid. 1H NMR (400 MHz, DMSO-d6) delta 2.21 (s, 3H), 5.79 (bs, 2H), 6.68-6.71 (d, 1H), 7.10-7.13 (dd, 1H), 7.15 (s, 1H). 13C NMR (DMSO-d6) delta 20.13, 93.99, 116.12, 118.94, 125.38, 132.32, 135.76, 150.21. MS 133 (MH+).

The synthetic route of 64113-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENOMYX, INC.; US2008/306053; (2008); A1;,
Nitrile – Wikipedia,
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Electric Literature of 25978-68-1, 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 25978-68-1 as follows.

To a solution of methyl 4-cyano-3-methylbenzoate (36 mg, 0.205 mmol) in 1,4-dioxane (0.5 mL) and water (0.500 mL), was added sodium hydrogen sulfide (0.019 mL, 0.616 mmol) and triethylamine hydrochloride (170 mg, 1.233 mmol). The reaction mixture was heated at 55 0C overnight. The reaction was allowed to cool and water was added. The mixture was extracted with EtOAc. The combined organic layers were dried (Na2SC^), filtered and the solvent was evaporated in vacuo to give the product as a yellow solid. LCMS calc. = 210.1; found = 210.2 (M+l)+. 1H NMR (500 MHz, CDCl3) 7.86 (s, 1 H); 7.84 (d, J = 8.1 Hz, 1 H); 7.42 (d, J= 7.9 Hz, 1 H); 7.16 (s, 2 H); 3.93 (s, 3 H); 2.51 (s, 3 H).

According to the analysis of related databases, 25978-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2007/79186; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts