Month: May 2021

185147-06-2, name is 3-Fluoro-2-methylbenzonitrile, 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. Recommanded Product: 185147-06-2

A solution of the compound 2A (50 g, 0.37 mol) in CCI4 (500 mL) was added the NBS (72.5 g, 0.408 mol) and the AIBN (1 .2 g, 0.037 mol), the reaction solution was refluxed for overnight, TLC indicated the reaction was completed, the reaction solution was filtered and concentrated in vacuum to give the crude product which was purified by flash silica chromatography eluting with petroleum ether/EtOAc (500:1 ) to give the desired compound 2B (30 g, yield: 40%) as a white solid.

The synthetic route of 185147-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; MARIGO, Mauro; KILBURN, John Paul; NIELSEN, Jacob; PUeSCHL, Ask; LANGGARD, Morten; JESSING, Mikkel; KEHLER, Jan; WO2013/45607; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 127510-95-6, name is Methyl 2-cyano-5-methoxybenzoate, 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 127510-95-6, COA of Formula: C10H9NO3

5′-Methoxy-spiro[cyclopropane-11 ‘-isoindol]-3′(2’H)-one5 To a flask containing 2-Cyano-5-methoxy-benzoic acid methyl ester (10.22 g, 53.4 mmol), titanium (IV) isopropoxide (17 g, 61 mmol) and diethyl ether (200 mL) was added a solution of 3 M ethyl magnesium bromide in diethyl ether (36 mL, 107 mmol) at 0 “C. The mixture was allowed to warm to room temperature over 3 hours upon which an aqueous solution of 1 N HCI (200 mL) was slowly added. The black mixture was filtered through 400 g Q of celite and the filtrate was concentrated and absorbed onto silica in order to perform chromatography (0-100 % ethyl acetate: hexanes) to yield 5′-Methoxy-spiro[cyclopropane-11’- isoindol]-3′(2’H)-one (3.9 g, 38 %) MS: ES M+1 190.1 (189.2).

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, Methyl 2-cyano-5-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
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Application of 508203-48-3,Some common heterocyclic compound, 508203-48-3, name is 2,3-Difluoro-4-methylbenzonitrile, molecular formula is C8H5F2N, 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 suspension of 2,3-difluoro-4-methylbenzonitrile (5.0 g, 32.6 mmol) in ethanol (1 1 1 ml_) at 25C was added hydroxylamine hydrochloride (4.5 g, 65.3 mmol). The reaction mixture was heated at 80C for 2 hours. After cooling to room temperature the volatiles were removed under reduced pressure thus affording a white solid that was used in the next step without purification. NMR (400 MHz, CDCIs) d ppm: 7.30 (m, 1 H), 6.95 (m, 1 H), 5.05 (brs, 2H), 2.30 (s, 3H).

The synthetic route of 508203-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; PITTERNA, Thomas; STIERLI, Daniel; RAJAN, Ramya; (85 pag.)WO2019/207058; (2019); A1;,
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57381-44-9, name is 5-Bromo-2-chlorobenzonitrile, 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. HPLC of Formula: C7H3BrClN

3.1.1 2-chloro-5-piperazin-1-yl-benzonitrile (V-1) 0.200 g tert-butyl piperazine-1-carbamidate, 0.235 g 5-bromo-2-chlorbenzonitrile, 0.013 g tris(dibenzylideneacetone)dipalladium(0), 0.018 g rac-BINAP and 0.145 g sodium-tert-butoxide are suspended in 5 ml anhydrous, degassed toluene and heated under argon at 80 C until no further reaction takes place. The reaction mixture is filtered through Celite and mixed with a saturated sodium chloride solution. The product is extracted with ethyl acetate, dried and evaporated to dryness. 0.450 g tert-butyl 4-(4-chloro-3-cyanophenyl)-piperazine-1-carbamidate are obtained as an oil. The product obtained and 2 ml trifluoroacetic acid are suspended in 3 ml dichloromethane. The reaction mixture is stirred at ambient temperature until no further reaction takes place and then evaporated to dryness. The residue is suspended in diethyl ether and the solid is suction filtered. 0.300 g (V-1) are obtained as the trifluoroacetate. Analytical HPLC-MS (method B): RT=1.02 min

The synthetic route of 57381-44-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/28441; (2011); A1;,
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Synthetic Route of 31603-77-7,Some common heterocyclic compound, 31603-77-7, name is 4-Biphenylacetonitrile, molecular formula is C14H11N, 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.

General procedure: To a solution of arylacetonitrile (10 mmol) (2-(4-bromophenyl)acetonitrile) in dried THF (10 mL), LDA (2.0 M in THF, 20 mL, 40 mmol) was added under N2 atmosphere in an ice-bath. The solution was stirred at 45 C for 1 h. After cooling the reaction mixture again to 0 C, iodomethane (60 mmol) was added drop wise. The reaction was stirred overnight at room temperature, quenched by 4 N HCl at 0 C and then diluted with Et2O. The phases were separated and the aqueous phase was extracted with Et2O (3 times). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4. After filtration and concentration, the crude acid was purified by flash column chromatography to give the desired product as a white or pale yellow solid. The next step of the hydrolysis was done by the reported procedures.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Biphenylacetonitrile, its application will become more common.

Reference:
Article; Hajipour, Abdol R.; Khorsandi, Zahra; Tetrahedron Letters; vol. 61; 3; (2020);,
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Some common heterocyclic compound, 53005-44-0, name is 2-Methoxy-6-methylbenzonitrile, molecular formula is C9H9NO, 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. Recommanded Product: 53005-44-0

To intermediate 145 (5.0 g, 34.03 mmol) in THF (50 ml), benzylmagnesium chloride (34 ml, 2M in THF, 68.02 mmol) was added at 0C over 30 min. and heated to reflux for 15 h. The reaction mixture was cooled to room temperature, 2N HC1 (200 ml) was added and again refluxed for 4h. The reaction mixture was cooled and extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate : petroleum ether to afford to afford the title compound as brown liquid (3.7 g , 45%). -NMR (delta ppm, CDCI3, 400 MHz): 7.30-7. 18 (m, 6H), 6.76 (m, 2H), 4.07 (s, 2H), 3.83 (s, 3H), 2.02 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 53005-44-0, its application will become more common.

Reference:
Patent; RHIZEN PHARMACEUTICALS SA; NAGARATHNAM, Dhanapalan; VAKKALANKA, Swaroop Kumar, V.S.; MUTHUPPALANIAPPAN, Meyyappan; VISWANADHA, Srikant; BABU, Govindarajulu; BHAVAR, Prashant, Kashinath; WO2012/151525; (2012); A1;,
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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. 3100-67-2, name is 1-Amino-2-naphthonitrile, A new synthetic method of this compound is introduced below., Safety of 1-Amino-2-naphthonitrile

A solution of [Intermediate 7-a] (18.5 g, 0.11 mol) in dimethyl formamide (200 mL) was stirred at 0 C. Drops of a solution of N-bromosuccinimide (20.1 g, 0.11 mol) in dimethyl formamide (100 mL) were slowly added over 1 hr. The reaction mixture was warmed to room temperature and stirred for 12 hrs. Following filtration with an excess of distilled water, the filtrate was washed with methanol and recrystallized in toluene and methanol to afford [Intermediate 7-b] (18.7 g): yield 69%.

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; SFC CO., LTD.; LEE, Chang-Hee; SEO, Hyun-JONG; YOON, Seo-Yeon; SHIM, So Young; KIM, Si-In; (214 pag.)US2018/233669; (2018); A1;,
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Reference of 874285-03-7,Some common heterocyclic compound, 874285-03-7, name is 3-Bromo-2-fluorophenylacetonitrile, molecular formula is C8H5BrFN, 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-(3-bromo-2-fluorophenyl)acetonitrile (800 mg, 3.7 mmol,1 eq.) and (S)-1- iodo-2-(2-iodoethoxy)propane (1.27 g, 3.74 mmol, 1 eq.) were dissolved in dimethyl sulfoxide (10 ml_). Sodium hydride (331 mg, 8.3 mmol, 2.2 eq.) was added to the reaction mixture and stirred for 1 h at room temperature. The reaction mixture was diluted with water (10 ml_) and ethyl acetate (10 ml_), and the layers were separated. The organic phase was washed with 1 M HCI (1×10 ml_), water (1×10 ml_) and brine (1×10 ml_). The organic phase was concentrated under vacuum to afford a diastereomehc mixture of (2S,4R)-4- (3-bromo-2-fluorophenyl)-2-methyl-tetrahydro-2H-pyran-4-carbonitrile and (2S,4S)-4-(3-bromo-2-fluorophenyl)-2-methyl-tetrahydro-2/-/-pyran-4- carbonitrile (1 :1 ). The diastereomehc mixture was separated by reverse phase chromatography (40 – 90% acetonithle-water) to obtain the title compound (252 mg, 23%) as a single isomer. Stereochemistry confirmed by NMR. [2SAR)- 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 1.26 (d, J=6.2 Hz, 3 H) 1.81 (dd, J=13.2, 11.0 Hz, 1 H) 2.08 – 2.26 (m, 3 H) 3.89 – 4.02 (m, 2H) 4.04 – 4.16 (m, 1 H) 6.99 – 7.13 (m, 1 H) 7.32-7.44 (m, 1 H) (s, 1 H) 7.51 – 7.63 (m, 1 H); LC/MS (M+H) = 298 (100%), 300 (98.5%). (2S,4S): 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 1.22 (d, J=6.2 Hz, 3 H) 2.05 (dd, J=14.5, 10.7 Hz, 1 H) 2.25-2.44 (m, 1 H) 2.49 – 2.63 (m, 2 H) 3.44 – 3.59 (m, 2H) 3.86 – 3.99 (m, 1 H) 7.02 – 7.13 (m, 1 H) 7.19-7.31 (m, 1 H) (s, 1 H) 7.53-7.64 (m, 1 H); LC/MS (M+H) = 298 (100%), 300 (98.5%).

The synthetic route of 874285-03-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); A1;,
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Reference of 191014-55-8, A common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, molecular formula is C8H6FNO, 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 the corresponding aryl fluoride (0.2 mmol) and the corresponding alcohol (0.200 mmol) in DMF (1 mL) is added 0.5 mL of 0.6 M slurry of sodium hydride (60%) in DMF (0.3 mmol). The resultant mixtures were shaken at room temperature for 48 hours. The reactions were quenched with water (0.5 mL). The solvent is evaporated in vacuo. To the concentrated reaction mixtures is added methylene chloride (3 mL) and water (2 mL). The organic layer is filtered through silica (0.5 g) solid phase extraction column and evaporated to yield material that was purified by reverse phase HPLC.

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; Pfizer Inc; US2009/170886; (2009); A1;,
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Reference of 867367-02-0, 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. 867367-02-0, name is 4-Fluoro-3,5-dimethylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 2-[4-Chloro-3-(4-cyano-2,6-dimethyl-phenoxy)-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide (I-55) step 1-A solution of 40 (0.600 g, 2.79 mmol), 3,5-dimethyl4-fluorobenzonitrile (41, 0.459 g, 3.07 mmol), K2CO3 (1.157 g, 8.37 mmol) and NMP (6 mL) was stirred and heated to 120 C. for 6 h. When the starting material was consumed the solution was cooled and acidified with 10% HCl and twice extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by SiO2 chromatography and eluted with an EtOAc/hexane gradient (100% hexane to 50% hexane) to afford 106a. Steps 2-4 were carried out as described in steps 7-9 of Example 1 which afforded I-55. Compound I-56 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 4-amino-2-methyl-benzenesulfonamide. Compound I-68 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 2-chloroaniline. Compound I-135 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 4-amino-2-chloro-benzenesulfonamide.

The synthetic route of 4-Fluoro-3,5-dimethylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2005/239880; (2005); A1;,
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