Day: March 8, 2021

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.5470-70-2, name is Methyl 6-methylnicotinate, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.Product Details of 5470-70-2

A solution of methyl 6-methylnicotinate (30 g, 198 mmol) in dry THF (150 mL) was added dropwise into a suspension of LiAlH4 (11 g, 289 mmol) in THF (200 mL) at 0 to – 5 ¡ãC. The grey suspension was stirred at RT for lh. The reaction mixture was cooled to -5 to 0 ¡ãC and water (11 mL) was added dropwise under nitrogen followed by slow addition of 15percent NaOH (11 mL) and water (33 mL). The reaction was warmed to RT and stirred for 30 min. at RT. The resulting suspension was filtered and the filtrate was concentrated under vacuum to give (6-methylpyridin-3-yl)methanol as a yellow oil (23 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5470-70-2, Methyl 6-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; CHAKRAVARTY, Sarvajit; HART, Barry, Patrick; JAIN, Rajendra, Parasmal; WO2011/103460; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5Br2N

Potassium hydride (105 mg) is added to an ice-cooled mixture of S,S- dimethylsulfoximine (34 mg) and tetrabutylammonium bromide (6 mg) in tetrahydrofuran (2 ml_) under an argon atmosphere and the resulting mixture is stirred at 0C for 1 h. 2-Bromo-6-bromomethyl-pyridine (101 mg) is added, the mixture is allowed to warmed to room temperature overnight and quenched with water. The organic phase washed with brine, dried over MgS04, and concentrated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol acetate 99:1?90:10) to give the title compound. LC (method 1 ): tR = 0.62 min; Mass spectrum (ESI+): m/z = 264, 266 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 83004-10-8.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; LANGKOPF, Elke; WAGNER, Holger; WO2015/7669; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131674-39-0, 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. 131674-39-0, name is 1-(2-Chloropyridin-3-yl)ethanol. A new synthetic method of this compound is introduced below.

Step 2 To a solution of 1-(2-chloropyridin-3-yl)ethanol (X) in dry acetone at -30 C. under nitrogen was added in portions chromium (VI) oxide (1.80 g, 18 mmol). The solution was further stirred 15 min at -30 C. and allowed to warm to room temperature. The solution was stirred for 3 h at room temperature before adding isopropanol (10 mL). The solution was made alkaline by slowly adding a saturated aqueous NaHCO3 solution. The solution was filtered through a bed of Celite. The solids were washed by DCM. The organic phase of the filtrate was separated and the aqueous phase extracted with DCM (2*50 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to yield 1-(2-chloropyridin-3-yl)ethanone (XI) as a brown liquid (0.72 g, 4.63 mmol, 77% yield). 1H NMR (CDCl3) delta ppm 2.71 (s, 3H), 7.35 (dd, J=7.63 Hz, J=4.80 Hz, 1H), 7.91 (dd, J=7.54 Hz, J=1.88 Hz, 1H), 8.55 (dd, J=4.71 Hz, J=1.88 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131674-39-0, 1-(2-Chloropyridin-3-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5467-69-6, Adding some certain compound to certain chemical reactions, such as: 5467-69-6, name is 6-Methoxy-2-methyl-3-nitropyridine,molecular formula is C7H8N2O3, 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 5467-69-6.

Preparation 7 2-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridine To 2-methoxy-5-nitro-6-methylpyridine (29.39 g, 175 mmol) dissolved in 300 mL of N,N-dimethylformamide was added dimethylformamide dimethylacetal (120 mL, 896 mmol) and triethylamine (1 mL). The bright red reaction mixture was heated at 120 C. for 2 hours, then concentrated in vacuo to provide 38.90 g of the title compound as a red solid, which was used in Preparation 13 without further purification.

According to the analysis of related databases, 5467-69-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US6358972; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-71-0, 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 1122-71-0, name is 6-Methyl-2-pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 11 : 2-(bromomethyl)-6-methylpyridi; (6-methyl-2-pyridinyl)methanol (ALDRICH, 300 mg, 2.436 mmol) were dissolved in 10 mL of anhydrous THF. Phosphorous tribromide (ALDRICH, 0.252 mL, 2.68 mmol) was added. Reaction mixture was stirred at room temperature overnight. Solvent was evaporated andresidue was purified by silica column chromatography using hexane:EtOAc as eluents to give a white solid. This solid was partitioned between EtOAc and distilled water (basified with NH3 (32%, aqueous). Organic layer was dried with MgS04 (anh). Solvent was evaporated to obtain the title compound (152 mg, 0.817 mmol, 33.5% yield). 1 H NMR (300 MHz, DMSO-cfe) delta ppm: 7.68 (t, 1 H), 7.33 (d, 1 H), 7.17 (d, 1 H), 4.62 (s, 2H), 2.44 (s, 3H). [ES+MS] m/z 186 (M).

According to the analysis of related databases, 1122-71-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; CASTRO PICHEL, Julia; FERNANDEZ MENENDEZ, Raquel; FERNANDEZ VELANDO, Esther Pilar; GONZALEZ DEL VALLE, Silvia; MALLO-RUBIO, Araceli; WO2012/49161; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73583-37-6 , The common heterocyclic compound, 73583-37-6, name is 4-Bromo-2-chloropyridine, molecular formula is C5H3BrClN, 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.

n-Butyllithium (7.8 mL of a 1.6 M solution with hexanes, 12 mmol) was added to a stirring solution of 4-bromo-2-chloropyridine (1.2 mL, 10 mmol, Alfa Aesar, Ward Hill, MA) and diethyl ether (52 mL) at -78 C. After 30 min, cyclobutanone (3.9 mL, 52 mmol) and water (50 mL) were added sequentially, and then the reaction mixture was warmed to room temperature, partitioned between ethyl acetate and more water, and the layers were separated. The organic material was dried (magnesium sulfate), silica gel (2.0 g) was added, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (40 g RediSep normal phase column, gradient elution of 0% to 30% ethyl acetate-hexane, Teledyne Isco, Lincoln, NE) to afford l-(2-chloro-4-pyridinyl)cyclobutanol (1.6 g).

The synthetic route of 73583-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53014-84-9, 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 53014-84-9, name is 2-Methyl-5-formylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution containing the product from Example 6F (0.150 g, 0.65 mmol) in a mixture of toluene (2.5 mL) and methanol (2.5 mL) was treated with the product from Example 13A (0.079 mL, 0.65 mmol), stirred at 50 C. for 16 hours, cooled to 25 C., treated with sodium borohydride (0.049 g, 1.29 mmol), stirred at 25 C. for 1 hour, quenched with 1N NaHCO3 and stirred for 1 hour, and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the concentrate (0.194 g) in 1,2-dichloroethane (10 mL) was treated with N,N-disuccinimidyl carbonate (0.20 g, 0.781 mmol) and triethylamine (0.11 mL, 0.789 mmol), stirred at 25 C. for 16 hours, and partitioned with 10% Na2CO3. The aqueous was extracted with additional chloroform. The combined organic phase was dried over MgSO4, filtered and concentrated. A solution of the concentrate (0.223 g) in dichloromethane (2.5 mL) was treated with trifluoracetic acid (2.5 mL), and the mixture was stirred at 25 C. for 2 hours. The solvent was concentrated to give the title compound (0.379 g) as the trifluoroacetic acid salt, which was used without further purification.

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 53014-84-9, 2-Methyl-5-formylpyridine.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69950-65-8 ,Some common heterocyclic compound, 69950-65-8, molecular formula is C8H7NO3, 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 3-bromo-2-phenyl-7-(trimethylsilyl)pyrazolo[1,5-a]pyridine (18, 550 mg, 1.59 mmol) in THF (4 mL) was added n-butyllithium (0.7 mL, 1.91 mmol, 2.6 mol/L solution in hexane) at -78 C. After stirring at -78 C for 0.5 h, a solution of methyl 6-formylpicolinate (527 mg, 3.19 mmol) in THF (4 mL) was added to the mixture at -78 C. The solution was stirred at room temperature for 1 h, and then the reaction was quenched by the addition of saturated aq. ammonium chloride. The mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (hexane:AcOEt = 4:1) to give the title compound 23 as a yellow oil (361 mg, 53%). 1H-NMR (400 MHz, CDCl3) delta 0.63 (9H, s), 4.21 (3H, s), 5.53 (1H, d, J = 2.4 Hz), 6.46 (1H, d, J = 2.4 Hz), 6.99 (1H, dd, J = 6.7, 1.8 Hz), 7.06 (1H, dd, J = 9.1, 6.7 Hz), 7.18 (1H, dd, J = 9.1, 1.8 Hz), 7.41-7.44 (2H, m), 7.62 (2H, tt, J = 7.3, 1.2 Hz), 7.86 (1H, t, J = 7.3 Hz), 8.03-8.07 (2H, m), 8.18 (1H, d, J = 7.3 Hz). IR (ATR) nmax 3417, 2953, 2898, 1720, 1586, 1516, 1439, 1356, 1314, 1243, 1138, 1079, 1029, 992, 892, 833, 759, 706, 634, 582, 506, 419 cm-1. MS (ESI) 432 [M+H]+. HRMS (ESI) calcd for C24H26N3O3Si [M+H]+ 432.17434, found 432.17514.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69950-65-8, its application will become more common.

Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Saito, Yoshifumi; Watanabe, Hiroyuki; Kondo, Tatsuhiro; Kondo, Atsushi; Kawamura, Naohiro; Tatani, Kazuya; Kohno, Yasushi; Tanaka, Nobuyuki; Seto, Shigeki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 17; (2017); p. 4044 – 4050;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 136888-21-6, 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. 136888-21-6, name is 2-Chloro-5-fluoro-3-nitropyridine, molecular formula is C5H2ClFN2O2, 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 high-pressure reaction vessel, 2,3-dichloro-5-fluoropyridine 85g (0.5 mol) was added to 200 mL of ammonia water, and the temperature was set at 180 C., and the reaction under high pressure was performed for 24 h. The reaction of the starting material was complete by TLC, and the solvent was swirled to obtain 2- Chloro-5-fluoro-3-aminopyridine 65g;Place 2-chloro-5-fluoro-3-aminopyridine 65 g (0.45 mol) in a 900 mL round-bottomed flask in acetonitrile, and add 450 mL of water buffer solution (0.6 M K2CO3-4¡Á10-4 M EDTA disodium salt). 350 mL (3 mol) of acetonitrile and 290 mL (3 mol) of a 30% H2O2 aqueous solution, and the reaction mixture was stirred at room temperature for 1 hour and extracted with ethyl acetate (3 x 300 mL). The organic layers were combined and dried over anhydrous Na2SO4. The solvent was removed to give a sufficiently pure product, 2-chloro-5-fluoro-3-nitropyridine, 65 g;To a solution of 65 g (0.35 mol) of 2-chloro-5-fluoro-3-nitropyridine in DMSO/H2O (mass ratio 9:1, 3500 mL) was added L-proline 230 g (2 mol), Na2CO3 210 g (2 mol), NaN3 230 g (3.5 mol), sodium ascorbate 350 g (1.75 mol) and CuSO4.5H2O 500 g (2 mol); the mixture was stirred in an oil bath at 70C for 24 hours, and then the mixture was poured into 5000 mL of ice water to give a solid product. Filter and crystallize to obtain 47g of 2-amino-5-fluoro-3-nitropyridine; add 2-amino-5-fluoro-3-nitropyridine to the aqueous solution of sulfuric acid, add a certain amount of chloroacetic acid, and heat to 120C. After TLC monitored the reaction of the raw materials, the reaction mixture was extracted with methylene chloride. The pH of the organic phase was adjusted to 7-8 with a saturated sodium carbonate solution, and the organic phase was concentrated to obtain 2-amino-5-fluoro-pyridine.

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 136888-21-6, 2-Chloro-5-fluoro-3-nitropyridine.

Reference:
Patent; Henan Longhu Biological Co., Ltd.; Mu Kairui; Lei Yansheng; (13 pag.)CN107827887; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7598-35-8, 2-Bromopyridin-4-amine, 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, HPLC of Formula: C5H5BrN2, blongs to pyridine-derivatives compound. HPLC of Formula: C5H5BrN2

To a cooled (0 C.) solution of 2,6-dichloro-4-iodobenzoyl chloride (70 mg, 0.21 mmol) in DMF (2 mL) was added NaH (17 mg, 0.42 mmol). The mixture was stirred for 10 minutes and then 2-bromopyridin-4-amine (40 mg, 0.23 mmol) was added. The resulting mixture was slowly warmed to 25 C., diluted with ethyl acetate (10 mL), quenched with water (1 mL), washed with saturated Na2CO3 and water, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel chromatography (Pet Ether/EtOAc=20:1 to 3:1) to afford N-(2-bromopyridin-4-yl)-2,6-dichloro-4-iodobenzamide (40 mg, 40% yield). LCMS (ESI) m/z: 470.9 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7598-35-8, 2-Bromopyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; US2010/317643; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem