Category: 58481-11-1

Synthetic Route of 58481-11-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 58481-11-1, name is Methyl 2-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-chloroisonicotinate (0.996 g, 5.80 mmol), potassium carbonate (1.042 g, 7.54 mmol), 4,4,5,5-tetramethyl-2-(3-methyl-4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (1.66 g, 5.80 mmol) and PdCl2 (dppf) (0.105 g, 0.15 mmol) were mixed in methanol (20 mL) in two microwave vials. The vials were capped and heated at 100° C. for 10 min in a single node microwave reactor. The solution was partitioned between water and ethyl acetate. The organic layer was isolated, dried over Na2SO4, filtered through celite and the solvent was evaporated. Automated column chromatography using the Biotage equipment. Gradient eluation using heptane-ethyl acetate, 0percent to 50percent. Methyl 2-(3-methyl-4-(trifluoromethyl)phenyl)-isonicotinate (1.22 g, 71percent) was isolated. 1H NMR (600 MHz, cdcl3) delta 2.57 (s, 3H), 3.99 (s, 3H), 7.70 (d, 1H), 7.81 (dd, 1H), 7.91 (d, 1H), 7.98 (s, 1H), 8.29 (s, 1H), 8.84 (d, 1H).

According to the analysis of related databases, 58481-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58481-11-1, Methyl 2-chloroisonicotinate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Methyl 2-chloroisonicotinate (4.5 g, 26.23 mmol), 4-fluorophenylboronic acid (4.51 g, 32.26 mmol), potassium carbonate (2.247 g, 16.26 mmol) and PdCl2 (dppf) (0.380 g, 0.52 mmol) were mixed in methanol (30 mL) in two 20 mL microwave vials. The vials were capped and heated at 100° C. for 10 min in a single node microwave reactor. The solids were removed by filtration and the filtrate evaporated to yield a dark red slurry. To the residue was added HCl (1.25 M in methanol, 100 mL). The mixture was stirred at 45° C. for 4 h, then concentrated. Satd NaHCO3 (100 mL) was added under ice cooling and extracted with DCM (3.x.100 mL) The combined organic phases were washed with brine, passed through a phase separator and evaporated to yield a brown solid. The crude was dissolved in MTBE (180 mL) and some solids were filtered off. Cooled with ice-water, hydrogen chloride (4 M in dioxane, 10 mL, 40 mmol) was added dropwise during stirring and a suspension was formed. The suspension was stirred at 0° C. for 10 min. The solid was collected by filtration and washed with MTBE to yield methyl 2-(4-fluorophenyl)isonicotinate hydrochloride (6.4 g, 91percent) as a beige solid. 1H NMR (400 MHz, cd3od) d 4.07 (s, 3H), 7.37-7.51 (m, 2H), 8.02-8.13 (m, 2H), 8.37 (dd, 1H), 8.71 (d, 1H), 8.97 (dd, 1H). MS m/z 232 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58481-11-1, Methyl 2-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); 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. 58481-11-1, name is Methyl 2-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H6ClNO2

Step 3 Preparation of 1-(2-Chloroisonicotinyl)-1,3-butanedione: To solution of methyl 2-chloroisonicotinate (12.0 g, 0.07 mol) and acetone (12.2 g, 0.21 mol) in 100 mL of dry THF at 35 C was added sodium methoxide portionwise. After heating the reaction mixture at reflux for 4 h, the solvent was removed. The residue was dissolved with 500 mL of water, acidified with acetic acid to pH=6 and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give 11.46 g (83percent yield) of product was a brown solid.

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, 58481-11-1, Methyl 2-chloroisonicotinate.

Reference:
Patent; Pharmacia Corporation; US6509361; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58481-11-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 58481-11-1, name is Methyl 2-chloroisonicotinate, molecular formula is C7H6ClNO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a dried flask was zinc powder (3.05 g, 46.69 mmol) suspended in anhydrous tetrahydrofuran (25 mL) under nitrogen. The resulting suspension was warmed to 60° C., then 1,2-dibromoethane (0.168 mL, 1.95 mmol) was added and stirred at that temperature for 15 min. It was cooled to room temperature, then chlorotrimethylsilane (0.2 mL, 1.58 mmol) was added and stirred at room temperature for 1 h 15 min. Then, 4-(bromomethyl)-2-fluoro-1-(trifluoromethyl)benzene (10 g, 38.91 mmol) in tetrahydrofuran (5 mL) was added in 6 equal portions every 10 minutes under ice-cooling. After complete addition the ice-bath was removed and the reaction mixture stirred at room temperature for 18 h. Then was stirring switched off to let the solids settle. The supernatant was used in next transformation. To a solution of methyl 2-chloroisonicotinate (5.15 g, 30 mmol) and Pd(PPh3)4 (0.693 g, 0.60 mmol) in tetrahydrofuran (40 mL) under nitrogen in a dried flask was added freshly prepared (3-fluoro-4-(trifluoromethyl)benzyl)zinc(II) bromide (12.55 g, 38.91 mmol) in tetrahydrofuran (50 mL). The resulting bright yellow mixture was heated to 60° C. for 2 h 20 min, then cooled to room temperature. The reaction was quenched by the addition of 10percent NH4Cl. It was diluted with ethyl acetate. After phase separation, the organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was suspended in 150 mL MTBE and sonicated, then the yellow insolubles were filtered off and washed with MTBE. The volume of the filtrate was increased to ca. 200 mL, then hydrogen chloride (7.50 mL, 30.00 mmol) (4M in dioxane) was added dropwise. A colorless precipitate formed. The resulting suspension was stirred for ca. 1 h, then sonicated for 2 min. The formed solid was collected and washed with MTBE and dried. The solid was dissolved in DCM and washed with 10percent K2CO3. After phase separation, the aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated. Methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)isonicotinate (8.26 g, 88percent) was isolated as a pale orange oil. 1H NMR (400 MHz, cdcl3) delta 3.94 (s, 3H), 4.24 (s, 2H), 7.06-7.18 (m, 2H), 7.52 (t, 1H), 7.69-7.75 (m, 2H), 8.68-8.75 (m, 1H). MS m/z 314 (M+H)+

According to the analysis of related databases, 58481-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58481-11-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 58481-11-1, name is Methyl 2-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-chloroisonicotinate (5.5 g, 32.05 mmol), (E)-4-fluorostyrylboronic acid (7.98 g, 48.08 mmol), potassium phosphate (3.93 mL, 48.08 mmol) and PdCl2 (dppf) (0.464 g, 0.64 mmol) were split into 5 equal portions and each portion was placed in a microwave reaction vessel. The vessels were evacuated and backfilled with nitrogen. Methanol (15 mL) was added to each vessel, the vessels were sealed and heated in a single node microwave reactor at 100° C. for 10 min each. The contents of the vessels was pooled and water and DCM were added, the phases separated and the aqueous layer was extracted with DCM. The combined organic layers were filtered through a phase separator and evaporated. The residue was purified by automated flash chromatography on a Biotage.(R). KP-SIL 340 g column. A gradient from 6:1 to 4:1 of EtOAc in heptane over 15 CV was used as mobile phase. (E)-Methyl 2-(4-fluorostyryl)isonicotinate (3.88 g, 47percent) was isolated. 1H NMR (400 MHz, cdcl3) delta 3.98 (s, 3H), 7.04-7.18 (m, 3H), 7.52-7.62 (m, 2H), 7.63-7.71 (m, 2H), 7.93 (s, 1H), 8.74 (d, 1H). MS m/z 258 (M+H)+

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 58481-11-1, Methyl 2-chloroisonicotinate.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58481-11-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 58481-11-1, name is Methyl 2-chloroisonicotinate, molecular formula is C7H6ClNO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

1. Synthesis of methyl 2-(thiazol-2-ylamino)isonicotinate A suspension of methyl 2-chloroisonicotinate (15.0 g, 87.42 mmol), 2-aminothiazole (10.50 g, 104.9 mmol), sodium carbonate (12.97 g, 122.4 mmol, 1.4 eq) and XANTPHOS (0.607 g, 1.049 mmol, 0.012 eq) in toluene (300 mL, bubbled with argon for 5 minutes) was bubbled again with argon for 5 additional minutes. Tris(dibenzylideneacetone)dipalladium (0) (0.320 g, 0.349 mmol, 0.004 eq) was then added to the suspension which was heated at 100° C. for 5 days. The mixture was cooled down to RT and filtered. The resulting solid was suspended in water and stirred for 1 hour. After filtration, the resulting solid was dried under vacuum overnight and afforded the title material (14.17, 69percent) as a solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 3.90 (3H, s), 7.07 (1H, d, J=3.54), 7.32 (1H, dd, J=5.31, 1.26 Hz), 7.43 (1H, d, J=3.79 Hz), 7.61 (1H, s), 8.48 (1H, d, J=4.55 Hz), 11.56 (1H, s). LC/MS (M+H)+: 236. HPLC ret. time (Condition A): 1.182 min.

According to the analysis of related databases, 58481-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; US2010/48581; (2010); 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.58481-11-1, name is Methyl 2-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Recommanded Product: Methyl 2-chloroisonicotinate

To a suspension of lithium aluminum hydride (221 mg) in Et2O (10.0 mL) cooled to -40C was added methyl 2-chloroisonicotinate (1.00 g) in Et2O (2 mL) dropwise and the mixture was stirred at -4 0C for 30 min and quenched with water. The aqueous layer was extracted with EtOAc three times. The combined organic layer was washed with aqueous saturated NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure to give (2-chloropyridin-4-yl)methanol (641 mg) as a pale brown solid.1HNMR (300 MHz, CDCl3, delta): 2.81-2.93 (m, IH), 4.72-4.80 (m, 2H), 7.17-7.26 (m, IH), 7.34-7.41 (m, IH), 8.30 (dd, J= 5.1, 0.6 Hz5 IH); ESI MS m/z 144 (M++., 100percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58481-11-1, Methyl 2-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; ARENA PHARMACEUTICALS, INC.; WO2006/35967; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58481-11-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 58481-11-1, name is Methyl 2-chloroisonicotinate, molecular formula is C7H6ClNO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of methyl 2-chloroisonicotinate (4.59 g, 26.7 mmol) in dry dioxane (120 mL),Pd(dppt) (2.18 g, 2.67 mmol) is added under argon. To this red-brown suspension 3-pentylzink (11.6 g, 53.5 mmol, 107 mL of a 0.5 M solution in THF) is added and the mixture is stirred at 100¡ãC for 18 h. The black solution is cooled to rt, diluted with EA (200 mL) and washed with water (100 mL) and 2 N aq. HCI. The washings are extracted four times with DCM (4×100 mL). The combined org. extracts are dried over MgSO4, filtered andconcentrated. The crude product is purified by MPLC on silica gel eluting with a gradient of EA in heptane to give methyl 2-(pentan-3-yl)isonicotinate (1.15 g, 21percent) as brownish oil containing a few percent of methyl 2-(pentan-2-yl)isonicotinate; LC-MS: tR = 0.62 mm; [M+1] = 208.30. This material is dissolved in THF (30 mL) and 25percent aq. HCI (25 mL) and the mixture is stirred at 70¡ãC for 18 h before it is concentrated and dried to give the title compound (467 mg, 37percent) as a beige solid; LC-MS: tR = 0.35 mi [M+1] = 194.28; 1HNMR (CD3OD): 8.74 (d, J = 5.2 Hz, 1 H), 7.97 (5, 1 H), 7.96 (d, J = 6.0 Hz, 1 H), 2.74-2.84 (m, 1 H), 1.71-1.91 (m, 4 H), 0.83 (t, J = 7.4 Hz, 6 H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 58481-11-1, Methyl 2-chloroisonicotinate.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; LESCOP, Cyrille; NAYLER, Oliver; STEINER, Beat; WO2014/141171; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58481-11-1, Methyl 2-chloroisonicotinate, 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, 58481-11-1, blongs to pyridine-derivatives compound. Recommanded Product: Methyl 2-chloroisonicotinate

To a stirred solution of methyl 2chloro isonicotinate (2 g, 0.012 mol) in toluene (20 mL) was added hexamethylditin (4.5 g, 0.014 mol), the mixture was degassed with argon for 10 minutes, then Pd(PPh3)4 (1.35 g, 0001 mol) was added, the mixture was degassed again for 5 minutes and the resulting reaction mixture was heated at 110¡ãC for 16h. The progress of the reaction was monitored by LCMS. The reaction mixture was cooled to RT, filtered through the Celite pad, washed with EtOAc and the filtrate was concentrated to get acrude compound. The crude compound was purified by column chromatography using neutral alumina and eluted with 5percentEtOAc/pet ether to afford the title compound (1.5 g, 42percent) as a colorless liquid.LCMS (method 1): R = 1.20 mm; m/z = 301 .99(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,58481-11-1, its application will become more common.

Reference:
Patent; ORYZON GENOMICS, S.A.; ORTEGA MUNOZ, Alberto; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; (176 pag.)WO2017/207813; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58481-11-1, Methyl 2-chloroisonicotinate, 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, name: Methyl 2-chloroisonicotinate, blongs to pyridine-derivatives compound. name: Methyl 2-chloroisonicotinate

In a dried flask was zinc powder (0.769 g, 11.76 mmol) suspended in anhydrous tetrahydrofuran (20 mL) under nitrogen. The resulting suspension was warmed to 60¡ã C., then 1,2-dibromoethane (0.042 mL, 0.49 mmol) was added and stirred at that temperature for 15 min. It was cooled to room temperature, then chlorotrimethylsilane (0.050 mL, 0.39 mmol) was added and stirred at room temperature for 1 h. Then, 1-(bromomethyl)-4-(trifluoromethoxy)benzene (2.5 g, 9.80 mmol) in tetrahydrofuran (5 mL) was added over 2 min, then stirring continued at room temperature for 22 h. The stirring was switched off to let the solids settle. The supernatant was used in next transformation. To a solution of methyl 2-chloroisonicotinate (4.80 g, 28 mmol) and Pd(PPh3)4 (0.647 g, 0.56 mmol) in tetrahydrofuran (50 mL) under nitrogen in a dried flask was added a freshly prepared solution of (4-(trifluoromethoxy)benzyl)zinc(II) bromide (12.56 g, 39.20 mmol) in tetrahydrofuran (90 mL). The resulting bright yellow mixture was heated to 60¡ã C. for 2 h 30 min, then cooled to room temperature. The reaction was quenched by the addition of 10percent aqueous NH4Cl. It was diluted with ethyl acetate. After phase separation, the organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was suspended in 50 mL MTBE and sonicated, then the yellow insolubles were filtered off and washed with MTBE. The volume of the filtrate was increased to ca. 150 mL, then 5 mL MeOH was added, followed by hydrogen chloride (4 M in dioxane) (7.00 mL, 28.00 mmol). A colorless precipitate formed, which then dissolved again. The solvents were evaporated. The residue was dissolved in ca. 15 mL DCM and then MTBE and heptanes were added. An oil had formed that was triturated and after a few minutes a solid started to form. It was sonicated and then stirred at room temperature for 20 min. The formed solid was collected and washed with MTBE and dried. The solid was dissolved in DCM and washed with 10percent K2CO3. After phase separation, the aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated. Methyl 2-(4-(trifluoromethoxy)benzyl)isonicotinate (8.04 g, 92percent) was isolated as a pale yellow oil. 1H NMR (400 MHz, cdcl3) delta 3.93 (s, 3H), 4.22 (s, 2H), 7.11-7.17 (m, 2H), 7.24-7.31 (m, 2H), 7.67-7.72 (m, 2H), 8.68-8.72 (m, 1H). MS m/z 312 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58481-11-1, Methyl 2-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem