Category: 135450-23-6

Adding a certain compound to certain chemical reactions, such as: 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, 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, 135450-23-6, blongs to pyridine-derivatives compound. Quality Control of 6-(Chloromethyl)-2-cyanopyridine

Reference Example 150-1 tert-Butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-2-(1-methylcyclopropyl)-2-oxoethyl]-5-methoxyphenyl}carbamate Under an argon atmosphere, to a solution of tert-butyl {5-methoxy-2-[2-(1-methylcyclopropyl)-2-oxoethyl]phenyl}carbamate (300 mg) in N,N-dimethylformamide (3.1 mL) was added sodium hydride (50-72% in oil, 50 mg) under ice-cooling, and the mixture was stirred for 1 hour. 6-(Chloromethyl)pyridine-2-carbonitrile (158 mg) was added thereto in one portion, and the mixture was gradually warmed to room temperature. 13 Hours later, to the reaction mixture were added a saturated aqueous ammonium chloride solution and water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (271 mg). 1H-NMR (CDCl3) delta ppm: 0.62-0.73 (2H, m), 1.22-1.30 (5H, m), 1.57 (9H, s), 3.21 (1H, dd, J=8.2, 15.7 Hz), 3.54 (1H, dd, J=6.7, 15.7 Hz), 3.78 (3H, s), 4.68-4.78 (1H, m), 6.54-6.61 (1H, m), 6.95 (1H, d, J=8.5 Hz), 7.18-7.25 (1H, m), 7.33-7.40 (1H, m), 7.48-7.55 (1H, m), 7.64 (1H, t, J=7.8 Hz), 7.82 (1H, br s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135450-23-6, its application will become more common.

Reference:
Patent; Tatani, Kazuya; Kondo, Atsushi; Kondo, Tatsuhiro; Kawamura, Naohiro; Seto, Shigeki; Kohno, Yasushi; US2013/317065; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, molecular formula is C7H5ClN2, molecular weight is 152.58, as common compound, the synthetic route is as follows.Quality Control of 6-(Chloromethyl)-2-cyanopyridine

Reference Example 149-1 tert-Butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-3-methyl-2-oxobutyl]-5-methoxyphenyl}carbamate Under an argon atmosphere, to a solution of tert-butyl [5-methoxy-2-(3-methyl-2-oxobutyl)phenyl]carbamate (337 mg) in N,N-dimethylformamide (4 mL) was added sodium hydride (50-72% in oil, 56 mg) under ice-cooling, and the mixture was stirred for 30 minutes. 6-(Chloromethyl)pyridine-2-carbonitrile (167 mg) was added thereto, followed by stirring for 1 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (271 mg). 1H-NMR (CDCl3) delta ppm: 0.91 (3H, d, J=6.5 Hz), 1.07 (3H, d, J=7.3 Hz), 1.57 (9H, s), 2.56-2.72 (1H, m), 3.18 (1H, dd, J=8.2, 15.9 Hz), 3.61 (1H, dd, J=6.8, 15.9 Hz), 3.77 (3H, s), 4.65-4.74 (1H, m), 6.58 (1H, dd, J=2.8, 8.7 Hz), 6.92 (1H, d, J=8.7 Hz), 7.22-7.29 (1H, m), 7.35 (1H, d, J=2.8 Hz), 7.46-7.60 (2H, m), 7.65 (1H, t, J=7.8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Tatani, Kazuya; Kondo, Atsushi; Kondo, Tatsuhiro; Kawamura, Naohiro; Seto, Shigeki; Kohno, Yasushi; US2013/317065; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 135450-23-6 ,Some common heterocyclic compound, 135450-23-6, molecular formula is C7H5ClN2, 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 stilTed solution of 1H-indole-3-carboxaldehyde (145.2mg, lmmol) and 6- (chloromethyl)picolinonitrile (167.8mg, l.lmmol) in 5.0 mL of MeCN was added Cs2CO3(980mg, 3mmol) at room temperature. The mixture was then heated to 80C and kept stirring for 3h. When 1H-indole-3-carboxaldehyde was consumed monitored by TLC, MeCN was evaporated. The residue was partitioned in 15 mL of water and 15 mL of ethyl acetate. The aqueous layer was extracted with ethyl acetate three times. The combined organic extracts were washed with brine, dried, and concentrated. The crudeproduct was purified by silica gel colunrn chromatography to give 6-((3 -formyl- 1 H-indol1-yl)methyl)picolinonitrile (214mg, 82% yield).ESI-MS mlz 262.1 [M+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. 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH, CHINESE ACADEMY OF SCIENCES; JIANG, Baishan; HU, Langxi; CUI, Yan; DING, Sheng; (29 pag.)WO2015/192343; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, molecular formula is C7H5ClN2, molecular weight is 152.58, as common compound, the synthetic route is as follows.category: pyridine-derivatives

General procedure: Reference Example 24 6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile [0267] To a solution of 5-methoxy-2-phenyl-1H-indole (200 mg) in N,N-dimethylformamide (5 mL) was added sodium hydride (dispersed in liquid paraffin, 50% or more, 45 mg) under ice-cooling. This mixture was stirred for 30 minutes at room temperature. Subsequently, 6-chloromethylpyridine-2-carbonitrile (216 mg) was added thereto, followed by stirring at 80C overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (228 mg). [0268] 1H-NMR (DMSO-d6) delta ppm: 3.77 (3H, s), 5.55 (2H, s), 6.55-6.65 (1H, m), 6.77 (1H, dd, J = 2.4, 8.8 Hz), 6.91 (1H, dd, J = 1.5, 7.4 Hz), 7.13 (1H, d, J = 2.4 Hz), 7.26 (1H, d, J = 8.8 Hz), 7.35-7.55 (5H, m), 7.85-7.95 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Kyorin Pharmaceutical Co., Ltd.; TATANI, Kazuya; KONDO, Atsushi; KONDO, Tatsuhiro; KAWAMURA, Naohiro; SETO. Shigeki; KOHNO, Yasushi; EP2669271; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 135450-23-6 ,Some common heterocyclic compound, 135450-23-6, molecular formula is C7H5ClN2, 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 commercially available chloride 30 (9.66 g,63.3 mmol) in DMF (400 mL) at ambient temperature was treatedwith potassium phthalimide (11.7 g, 63.3 mmol). After stirring for5 h, the mixture was concentrated under vacuum. The remainingmixture was taken up in H2O (200 mL) and was filtered to collectthe solid. The solid was washed with H2O (100 mL) and THF(100 mL) to obtain the desired phthalimide derivative (11.5 g,69%) and was moved forward without further purification. To asolution of the crude phthalimide derivative (5.84 g, 22.2 mmol)in THF/MeOH (200 mL, 1:1, v/v) at ambient temperature was treatedwith hydrazine monohydrate (1.18 mL, 24.4 mmol). After 2 h,1.0 M HCl (24.5 mL) was added to the mixture and was stirredfor another 3 h before concentrating the reaction mixture undervacuum. The remaining residue was taken up in H2O (200 mL)and the unwanted solid was removed through filtration. The filtratewas concentrated and placed under vacuum to remove theremaining H2O. The crude solid was taken up in CH2Cl2 (175 mL)and triethylamine (9.28 mL, 66.6 mmol) and Boc2O (4.86 g,24.4 mmol) was added. After stirring for 12 h at room temperature,the reaction was quenched with a saturated solution of NaHCO3(200 mL), extracted with CH2Cl2 (3 150 mL), dried over MgSO4,and concentrated under reduced pressure. The residue was purifiedusing flash chromatography (10-45% ethyl acetate in hexanes)to provided the aryl pyridine ?IN? fragment (2.24 g, 43%): 1H NMR(CDCl3, 400 MHz) d 7.78 (t, J = 7.6 Hz, 1H), 7.56 (d, J = 7.6 Hz, 1H),7.49 (d, J = 8.0 Hz, 1H), 5.51 (s, 1H), 4.44 (d, J = 5.6 Hz, 2H), 1.43(s, 9H); 13C NMR (CDCl3, 100 MHz) 160.1, 155.9, 137.6, 133.0,127.0, 125.1, 117.1, 79.9, 45.5, 28.3; IR (neat) 3347, 2979, 2934,2239, 1699, 1518, 1453, 1250, 1170, 862; HRMS (ESI) m/z calcdfor C12H15N3NaO3 [M+Na]+ 256.1062, found 256.1062.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135450-23-6, its application will become more common.

Reference:
Article; Clausen, Dane J.; Smith, William B.; Haines, Brandon E.; Wiest, Olaf; Bradner, James E.; Williams, Robert M.; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 5061 – 5074;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 135450-23-6 , The common heterocyclic compound, 135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, molecular formula is C7H5ClN2, 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 1-(1-methyl-1 /-/-tetrazol-5-yl)-1,3-dihydro-2H-benzo[d]imidazole-2-thione H (26 mg, 0.1 1 mmol) in dry DMF (1 mL) was treated with a solution of A/-(6-(bromomethyl)pyridin- 2-yl)-2,2-difluoro-2-phenoxyacetamide E (49 mg, 0.14 mmol) in dry THF (0.7 mL) and caesium carbonate (60 mg, 0.18 mmol) was added. The mixture was stirred at RT for 100 min then diluted with EtOAc (20 mL), washed with water (3 x 20 mL) and brine, dried (MgSCU) and chromatographed on silica (4 g Puriflash cartridge) eluting with 0-50% EtOAc / PE to give 2,2-difluoro-/V-(6-(((1-(1-methyl-1H-tetrazol-5-yl)-1H-benzo[d]imidazol-2- yl)thio)methyl)pyridin-2-yl)-2-phenoxyacetamide 1 (48 mg, 84%) as a colourless gum. 1H N MR (500 MHz, CDC) delta 8.90 (s, 1H), 8.13 (d, J = 8.3 Hz, 1H), 7.77 (d, J = 8.0 Hz, 1H), 7.74 – 7.68 (m, 1H), 7.45 – 7.33 (m, 3H), 7.32 – 7.26 (m, 5H), 7.07 – 7.00 (m, 1H), 4.67 (s, 2H), 3.92 (s, 3H); LCMS (method B): 3.28 min (509, MH+). Potassium carbonate was used instead of caesium carbonate

The synthetic route of 135450-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDAG CROP PROTECTION LTD; URCH, Christopher, John; BUTLIN, Roger, John; CHRISTOU, Stephania; BOOTH, Rebecca, Kathryn; (111 pag.)WO2018/130838; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 135450-23-6

[00369] 6-((((tert-Butoxy)carbonyl)amino)methyl)picolinonitrile (P31): To a solution of commercially available chloride P30 (9.66 g, 63.3 mmol) in DMF (400 mL) at ambient temperature was treated with potassium phthalimide (11.7 g, 63.3 mmol). After stirring for 5 h, the mixture was concentrated under vacuum. The remaining mixture was taken up in H20 (200 mL) and was filtered to collect the solid. The solid was washed with H20 (100 mL) and THF (100 mL) to obtain the desired phthalimide derivative (11.5 g, 69%) and was moved forward without further purification. To a solution of the crude phthalimide derivative (5.84 g, 22.2 mmol) in THF/MeOH (200 mL, 1:1, v/v) at ambient temperature was treated with hydrazine monohydrate (1.18 mL, 24.4 mmol). After 2 h, 1.0 M HC1 (24.5 mL) was added to the mixture and was stirred for another 3 h before concentrating the reaction mixture under vacuum. The remaining residue was taken up in H20 (200 mL) and the unwanted solid was removed through filtration. The filtrate was concentrated and placed under vacuum to remove the remaining H20. The crude solid was taken up in CH2C12 (175 mL) and triethylamine (9.28 mL, 66.6 mmol) and Boc2O (4.86 g, 24.4 mmol) was added. After stirring for 12 h at room temperature, the reaction was quenched with a saturated solution of NaHCO3 (200 mL), extracted with CH2C12 (3 x 150 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified using flash chromatography (10% to 45% ethyl acetate in hexanes) to provide the aryl pyridine ?IN? fragment (2.24 g, 43%): ?H-NMR (CDC13, 400 MHz) oe 7.78 (t, J = 7.6 Hz, 1H), 7.56 (d, J = 7.6 Hz, 1H), 7.49 (d, J= 8.0 Hz, 1H), 5.51 (s, 1H), 4.44 (d, J= 5.6 Hz, 2H), 1.43 (s, 9H); ?3C-NMR (CDC13, 100 MHz) 160.1, 155.9, 137.6, 133.0, 127.0, 125.1, 117.1, 79.9, 45.5, 28.3; JR (neat) 3347, 2979, 2934, 2239, 1699, 1518, 1453, 1250, 1170, 862; HRMS (ESI) mlz calcd for C12H15N3NaO3 [M+Na1 256.1062, found 256.1062.

The synthetic route of 135450-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COLORADO STATE UNIVERSITY RESEARCH FOUNDATION; DANA-FARBER CANCER INSTITUTE, INC.; UNIVERSITY OF NOTRE DAME DU LAC; WILLIAMS, Robert, M.; BRADNER, James, E.; CLAUSEN, Dane; WIEST, Olaf, G.; NEWKIRK, Tenaya, L.; BOWERS, Albert, A.; GUERRA, Jennifer, Marie; (144 pag.)WO2016/144665; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, 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, 135450-23-6, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5ClN2

Charge Cl-nitrile (180 g) into a rector containing THF (540 g). Charge NaT (185.7 g) to the reactor and stirred at 50 C. After reaction completion, the reactor is cooled to 0 C. In another reactor, charge t-BuOK (145.6 g) and THF (320 g). Add (S)-tetrahydrofuran-3-ol (311.9 g) into the reactor while maintaining internal temperature below 50 Cto deprotonate the alcohol. Stir until t-BuOK dissolves. Add THF-OK / THF solution into 6-(iodomethyl)picolinonitrile solution (compound 6) while maintaining internal temperature below 10 C. Stir at room temperature until reaction completion. Concentrate the solution to remove THF solvent. Add ethyl acetate (630 g) and wash by water (420 g). Extract water phase by ethyl acetate (630 g). Combine organic layer and concentrate to obtain oil crude 374 g. The residue was distilled under vaccum (P=3-4 torr, internal temperature 174 C to 188 C) to obtain (S)-6-(((tetrahydrofuran-3-yl)oxy)methyl)picolinonitrile (compound 7) as an oily product (204g, >96% purity; 74% yield)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135450-23-6, its application will become more common.

Reference:
Patent; CORVUS PHARMACEUTICALS, INC.; BY, Kolbot; JONES, William, Benton; WOLFE, Bradley, Hamilton; (131 pag.)WO2018/183965; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 6-(Chloromethyl)-2-cyanopyridine

Intermediate HU (1754) 6-((2-Bromophenoxy)methyl)picolinonitrile (1755) To a sealable 4 mL vial, containing 6-(chloromethyl)picolinonitrile (100 mg, 0.66 mmol) and 2-bromophenol (113 mg, 0.66 mmol), were added Cs2CO3 (320 mg, 0.98 mmol) and acetonitrile (1.7 mL). The vial was then heated at 80 Celsius for 15 hours. The reaction was then diluted with ethyl acetate, filtered through a celite plug and concentrated to dryness. The material was used without further purification. 1H NMR (500 MHz, CDCl3) delta 8.02-7.93 (m, 1H), 7.93-7.85 (m, 1H), 7.65-7.59 (dd, J=7.7, 1.1, 1H), 7.58-7.53 (dd, J=7.9, 1.6, 1H), 7.29-7.22 (m, 1H), 6.93-6.90 (dd, J=8.3, 1.3, 1H), 6.90-6.86 (m, 1H), 5.23 (s, 2H).

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, 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Bacani, Genesis M.; Eccles, Wendy; Fitzgerald, Anne E.; Goldberg, Steven D.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Lee-Dutra, Alice; Liu, Jing; McClure, Kelly J.; Meduna, Steven P.; Pippel, Daniel J.; Rosen, Mark D.; Sales, Zachary S.; US2015/259357; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 6-(Chloromethyl)-2-cyanopyridine

Intermediate HU (1754) 6-((2-Bromophenoxy)methyl)picolinonitrile (1755) To a sealable 4 mL vial, containing 6-(chloromethyl)picolinonitrile (100 mg, 0.66 mmol) and 2-bromophenol (113 mg, 0.66 mmol), were added Cs2CO3 (320 mg, 0.98 mmol) and acetonitrile (1.7 mL). The vial was then heated at 80 Celsius for 15 hours. The reaction was then diluted with ethyl acetate, filtered through a celite plug and concentrated to dryness. The material was used without further purification. 1H NMR (500 MHz, CDCl3) delta 8.02-7.93 (m, 1H), 7.93-7.85 (m, 1H), 7.65-7.59 (dd, J=7.7, 1.1, 1H), 7.58-7.53 (dd, J=7.9, 1.6, 1H), 7.29-7.22 (m, 1H), 6.93-6.90 (dd, J=8.3, 1.3, 1H), 6.90-6.86 (m, 1H), 5.23 (s, 2H).

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, 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Bacani, Genesis M.; Eccles, Wendy; Fitzgerald, Anne E.; Goldberg, Steven D.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Lee-Dutra, Alice; Liu, Jing; McClure, Kelly J.; Meduna, Steven P.; Pippel, Daniel J.; Rosen, Mark D.; Sales, Zachary S.; US2015/259357; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem