Month: January 2021

Related Products 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.

Example 57 3′-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-fluoro-3-biphenylcarbonitrile 3-Bromo-5-fluorobenzonitrile (5.00 g, 25.0 mmol), Pd(OAc)2 (0.15 g), PPh3 (0.60 g) and K2CO3 (5.18 g, 37.5 mmol) were dissolved in dioxane (60 mL). The mixture was heated at 70 C. for 30 min, then [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (7.99 g, 30.0 mmol) was added. The mixture reaction was stirred at reflux overnight. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (50 mL) and brine (50 mL). And the organic layer was dried over Na2SO4. The product 3′-({[(1,1-dimethylethyl) (dimethyl)silyl]oxy}methyl)-5-fluoro-3-biphenylcarbonitrile (5.10 g, 60%) was purified by flash column chromatography. 1H NMR (400 MHz, CDCl3): delta 7.67 (t, J=5.2 Hz, 1H), 7.54-7.32 (m, 5H), 4.81 (s, 2H), 0.94 (s, 9H), 0.13 (s, 6H).

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

Reference:
Patent; Glaxo Group Limited; US2009/197871; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 77-57-6, 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 77-57-6 as follows.

EXAMPLE 10 N6-((1-Phenylcyclopentyl)methyl)adenosine (1-Phenylcyclopentyl)methylamine is prepared as its hydrochloride salt, m.p. 185-6 C. from 1-phenylcyclopentane carbonitrile as described in Example 11. The above amine hydrochloride (5.0 g, 24 mmol) is reacted with 6-chloropurine riboside (6.8 g, 24 mmol) as described in Example 11 infra to give after column chromatography N6-((1-phenylcyclopentyl)methyl)adenosine (3.80 g, 37%) as a solid white foam m.p. 74-8 C. Found: C, 59.02; H, 5.94; N, 15.25%. C22 H27 N5 O4 calculated requires: C, 62.12; H, 6.35; N, 16.47%. C22 H27 N5 O4 0.25 CHCl3 requires C, 58.69; H, 6.03; N, 15.38%.

According to the analysis of related databases, 77-57-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert Company; US4755594; (1988); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 60710-80-7, These common heterocyclic compound, 60710-80-7, name is 3-Amino-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.

A solution of 4-(pyridin-2-ylmethoxy)benzoyl chloride hydrochloride (644 mg, 2.60 mmol) and 3-amino-4-methylbenzonitrile (515 mg, 3.90 mmol) in pyridine was stirred for 16h. Concentration of the reaction mixture under reduced pressure afforded a crude residue, which was purified using ISCO MPLC (40-100% EtOAc/hexane) to yield the title compound. MS (M+H+) = 344.

Statistics shows that 3-Amino-4-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 60710-80-7.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27746; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

A four-necked flask equipped with stirrer and thermometer was charged with 250.0 g of a solution of 50.0 g (0.146 mol) of ()-4- [4-dimethylamino-l- (4′-fluorophenyl)-l- hydroxybutyl] -3-hydroxymethylbenzonitrile in toluene, and the temperature thereof was controlled so as to be [40C.] Then, 11.5 g (0.146 mol) of pyridine, 33.2 g (0.291 mol) of vinyl butyrate, 17.8 g (0.146 mol) of benzoic acid, and 10.0 g of an immobilized enzyme (Novozym 435) was added into the above mixture. The reaction mixture was stirred at [40C] for 20 hours under a slight flow of nitrogen, and then stirring was stopped. The enzyme was filtrated from the reaction mixture with Kiriyama funnel, and washed with 108 g of toluene. As a result, a toluene layer containing [(S)-4- [4-DIMETHYLAMINO-1- (4′-FLUOROPHENYL)-1-HYDROXYBUTYL]-] 3-hydroxymethylbenzonitrile (22.0 g, 0.064 mol, yield: 44.0%, optical purity: 99.0% [EE),] benzoic acid salt was obtained. The combined toluene layer was washed three times with water (500 ml x 3) at [60C,] and an aqueous layer containing [(S)-4- [4-DIMETHYLAMINO-L- (4′-FLUOROPHENYL)-L-] hydroxybutyl]-3-hydroxymethylbenzonitrile (21.0 g, 0.0614 mol, extraction yield: 96%), benzoic acid salt was obtained.

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; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 75344-77-3,Some common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

In a microwave vial, methyl 2-((S)-6-((R)-7-fluoro-4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-2,3-dihydro-1 H-inden-1 -yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (200 mg), 4-bromo-3,5-dimethylbenzonitrile (90 mg), K3PO4 (273 mg), Palladium-(ll)- acetate (10 mg) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (S-Phos) (17 mg) are suspended in toluene (10 mL) and water (2 mL) and purged for 10 minutes with argon. The vial is sealed and the mixture is stirred at 100C for 4 hours. After cooling to ambient temperature the mixture is partitioned between ethyl acetate and water. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10) to give the title compound. Yield: 85 mg; LC (method 19): tR = 1 .52 min; Mass spectrum (EST): m/z = 471 [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 4-Bromo-3,5-dimethylbenzonitrile, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144098; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 79463-77-7, 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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 3,4-difluoroaniline (646 mg, 5 mmol) in isopropanol (10 mL) was added diphenyl cyanocarbonimidate (1.19 g, 5 mmol) and the suspension was stirred at room temperature over night. The precipitate was filtered off, washed with isopropanol and dried under reduced pressure to yield the title compound as a white solid (1.18 g, 86%).MS ISP (m/e): 274.1 (100) [(M+H)+].1H NMR (DMSO-D6, 300 MHz): 5(ppm) = 10.92 (s, 1H), 7.65 (m, 1H), 7.43 (m, 3H), 7.29 (m, 4H).

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAUMANN, Karlheinz; FLOHR, Alexander; GOETSCHI, Erwin; GREEN, Luke; JOLIDON, Synese; KNUST, Henner; LIMBERG, Anja; LUEBBERS, Thomas; THOMAS, Andrew; WO2011/101304; (2011); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, 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 19924-43-7, category: nitriles-buliding-blocks

Production of l-(3- methoxyphenyl ) cyclopropanecarbonitrile60% Sodium hydride (2.72 g) was suspended in N, N- dimethylformamide (80 mL) and the mixture was cooled to00C. A solution of ( 3-methoxyphenyl) acetonitrile (4.00 g) in N, N-dimethylformamide (20 mL) was added dropwise to the mixture and the mixture was stirred at 00C for 1 hr. 1 , 2-Dibromoethane (3.5 mL) was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 17 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (hexane : ethyl acetate=100 : 0-?80 : 20 ) to give the title compound (2.76 g) as a yellow oil.1H-NMR (CDCl3) delta: 1.36-1.44 (2H, m) , 1.67-1.75 (2H, m) , 3.81 (3H, s), 6.77-6.89 (3H, m) , 7.21-7.29 (IH, m)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3-Methoxyphenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/64045; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 766-84-7, name is 3-Chlorobenzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-Chlorobenzonitrile

EXAMPLE 13; 5-(1-chloroethyl)-3-(3-chlorophenyl)-1,2,4-oxadiazole; (i) 3-chloro-N’-hydroxybenzenecarboximidamide; Sodium hydroxide (8.2 g in 50 mL water) and hydroxylamine hydrochloride (16 g in 20 mL water) were added to a solution of 3-chloro-benzonitrile (28 g, 203.5 mmol) at 80 C. in ethanol (50 mL). The resulting mixture was stirred for 2 h. at 80 C. The solvent was removed in vacuo. to afford the title compound (29.82 g, 85.9%). 1H NMR (300 MHz, CDCl3): delta (ppm) 7.65 (s, 1H), 7.52 (d, 1H), 7.41 (d, 1H), 7.35 (t, 1H), 4.86 (br, 2H), 1.68 (br, 1H).

The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; NPS PHARMACEUTICALS, INC.; US2007/37820; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 17823-40-4,Some common heterocyclic compound, 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile, molecular formula is C7BrF4N, 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 4-bromo-2,3,5,6-tetrafluorobenzonitrile (2.2 g, 5.53 mmol), 2-cyanopyridine-5-boronic acid pinacol ester (2.0 g, 5.53 mmol), Pd2(dba)3 (0.18 g, 0.2 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.16 g, 0.4 mmol) and K3PO4 (2.2 g, 10 mmol) in anhydrous toluene (100 ml) was degassed and heated at 115 C for 16 hours. The resulting mixture was poured into ethyl acetate (100 ml), after filtered off precipitate, the solution was loaded on silica gel and purified by flash column using eluents of ethyl acetate/hexane (10% to 30%). The desired fractions were collected and concentrated to give white solid (Compound25) (0.18 g, in 6% yield).

The synthetic route of 17823-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, SHIJUN; BASIAGO, ADAM; (86 pag.)JP2016/526025; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, A new synthetic method of this compound is introduced below., Product Details of 327-74-2

81.70 g (439 mmol) 4-amino-3-trifluoromethyl-benzonitrile are dissolved in 1000 ml of methanol, cooled to 0 C. Within 1.2 hours hydrochloric acid is added in gaseous form. Then the reaction mixture is refluxed for 5 hours with stirring, then diluted with water, cooled to 3 C. and suction filtered. The precipitate is washed with water and dried. Yield: 73.10 g (76% of theoretical)

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; Breitfelder, Steffen; Maier, Udo; Hoenke, Christoph; Joergensen, Anne T.; Pautsch, Alexander; Brandl, Trixi; Grauert, Matthias; Hoffmann, Matthias; Scheuerer, Stefan; Erb, Klaus; Pieper, Michael; Pragst, Ingo; US2007/238730; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts