Month: April 2022

Reference of 1235036-15-3, 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 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows.

[000594] To a solution of tert-butyl 3-bromo-6-chloropicolinate (5.92 g) in tetrahydrofuran (60 mL)and water (30 mL) was added the crude Example 1.20.1 (4.44 g), l,3,5,7-tetramethyl-6-phenyl- 2,4,8-trioxa-6-phosphaadamante (1.5 g), tris(dibenzylideneacetone)dipalladium(0) (927 mg) and Kappa3RhoOmicron/ FontWeight=”Bold” FontSize=”10″ (22 g). The mixture was stirred at reflux overnight, cooled, diluted with ethyl acetate (800 mL) and washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography, eluting with 20% ethyl acetate in heptane followed by 5% methanol in dichloromethane, to give the title compound. MS (ESI) m/e 531.1 (M+H)+.

According to the analysis of related databases, 1235036-15-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; TAO, Zhi-Fu; DOHERTY, George; WANG, Xilu; SULLIVAN, Gerard M.; SONG, Xiaohong; KUNZER, Aaron R.; WENDT, Michael D.; MARIN, Violeta L.; FREY, Robin R.; CULLEN, Steve C.; WELCH, Dennie S.; SHEN, Xiaoqiang; BENNETT, Nathan B.; HAIGHT, Anthony R.; ACKLER, Scott L.; BOGHAERT, Erwin R.; SOUERS, Andrew J.; JUDD, Andrew S.; (623 pag.)WO2016/94509; (2016); 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.62135-58-4, name is Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate, molecular formula is C9H9N3O2, molecular weight is 191.19, as common compound, the synthetic route is as follows.Recommanded Product: Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate

a [1,2,4]Triazolo[1,5-a]pyridin-2-ylmethanol To ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (prepared as described in J. Chem. Soc., Perkin Trans. 1, 1976, 2166) (0.67 g, 3.5 mmol) in THF (10 ml) was added lithium borohydride (78 mg, 3.6 mmol) and the mixture was stirred at room temperature under nitrogen overnight. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel, eluding with 2.5 to 5% methanol in dichloromethane. The resultant solid was recrystallized from ethyl acetate, yielding [1,2,4]triazolo[1,5-a]pyridin-2-ylmethanol as a white solid (0.054 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62135-58-4, Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US6476030; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53174-98-4 ,Some common heterocyclic compound, 53174-98-4, molecular formula is C8H5NOS, 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 compound B-132 (3.4 g, 21 mmol) in anhydrous ethanol (50 mL) was added hydroxylamine hydrochloride (4.4 g, 63 mmol) and potassium carbonate (8.7 g, 63 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. On completion, the mixture was filtered and washed with ethanol. The filtrate was concentrated in vacuo and purified by silica gel column chromatography [petroleum ether : ethyl acetate = 20: 1 ] to give compound B-133 (3.0 g, 81 % yield) as a yellow solid. LCMS: (ES+) m/z (M+H)+ = 1 79.1 , tR=0.543.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53174-98-4, its application will become more common.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7112-38-1, 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 7112-38-1, name is 3-(Hydrazinylmethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-cyclobutyl-3-oxo-propionitrile (3.3 g, 32 mmol) in ethanol (100 mL) was added Example 85 A (3.9 g, 32 mmol) at rt. The solution was heated under reflux for 4 h. After cooling, the reaction mixture was concentrated and the residue was separated by flash chromatography (silica gel, 0-15% gradient MeOH in CH2Cl2) to give Example 85B (6.8 g). Yield: 93%. MS (DCI): m/z 229 (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 7112-38-1, 3-(Hydrazinylmethyl)pyridine.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/95628; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine. A new synthetic method of this compound is introduced below., SDS of cas: 89510-90-7

The residue obtained in the 1st step and a sodium methoxide solution (5M methanol solution) (5 ml) were added to a tube and the tube was sealed, followed by stirring at 170C for 3 hours. The reaction solution was adjusted to room temperature. Sodium hydroxide (49 mg) was added, followed by stirring at 170C for 1 hour. The reaction solution was adjusted to room temperature, the solvent was distilled away under reduced pressure, and a saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate. Subsequently, the resultant was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane : ethyl acetate = 4:1 to 1:1), and yellow oily matter of 3-fluoro-2-methoxypyridin-4-amine (27 mg) was thus obtained. MS (ESI m/z): 143 (M+H) RT (min): 0.41

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, 89510-90-7, 2-Chloro-5-fluoro-4-pyridinamine.

Reference:
Patent; FUJIFILM Corporation; FUJIWARA, Hideyasu; SATO, Kimihiko; MIZUMOTO, Shinsuke; SATO, Yuichiro; KURIHARA, Hideki; KUBO, Yohei; NAKATA, Hiyoku; BABA, Yasutaka; TAMURA, Takashi; KUNIYOSHI, Hidenobu; HAGIWARA, Shinji; YAMAMOTO, Mari; (630 pag.)EP2589592; (2018); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73406-50-5 ,Some common heterocyclic compound, 73406-50-5, molecular formula is C8H9NO3, 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.

Step 2 A mixture of ethyl 3-hydroxypicolinate (15 g, 900 mmol), tributylsilyl chloride (16.23 g, 110 mmol), imidazole (8.0 g, 120 mmol) in methylene chloride was stirred overnight under a nitrogen atmosphere. Water was added and the methylene chloride layer was separated and concentrated in vacuo. Purification on a silica gel column using ethyl acetate-hexane (1:4) as the eluant gave ethyl 3-(tributylsilyloxy)picolinate as a solid (20 g).

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. 73406-50-5, Ethyl 3-hydroxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Syntex (U.S.A.) LLC; US6316464; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211518-35-2, 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. 1211518-35-2, name is Methyl 6-chloro-5-(trifluoromethyl)picolinate, molecular formula is C8H5ClF3NO2, 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.

A mixture of methyl 6-chloro-5-(trifluoromethyl)pyridine-2-carboxylate (see procedure 2, step B) (200 mg; 0.83 mmol), morpholine (73 muL; 0.83 mmol); N,N-diisopropylethylamine (159 muL; 0.92 mmol) and 3 mL of dimethyl sulfoxide is stirred for 1 hour at 120C. The reaction is quenched with methanol, filtered and purified by reverse phase chromatography-HPLC (modifier: trifluoroacetic acid). (0398) Yield: 110 mg (45 % of theory) (0399) Mass spectrometry (ESI+): m/z = 291 [M+H]+ (0400) HPLC (Method 3): Retention time = 1.021 min

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 1211518-35-2, Methyl 6-chloro-5-(trifluoromethyl)picolinate.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; TRIESELMANN, Thomas; GODBOUT, Cedrickx; HOENKE, Christoph; VINTONYAK, Viktor; (130 pag.)WO2019/149660; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 130473-26-6, 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 130473-26-6 as follows.

1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde (500 mg, 3.42 mmol) is dissolved in 1.5 ml formic acid. The solution is cooled in an ice bath, is treated drop-wise with 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol), is stirred 1 h in an ice bath, and allow to stand overnight at 5 C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is combined with 7 ml water, is diluted with 3 ml 2N NaOH, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to give 370 mg (67%) of 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. HRMS (FAB) calcd for C8H6N2O2+H: 163.0508, found 163.0507 (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,130473-26-6, its application will become more common.

Reference:
Patent; Wishka, Donn G.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Reitz, Steven Charles; Rauckhorst, Mark R.; Groppi JR., Vincent E.; US2003/105089; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73455-13-7, 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. 73455-13-7, name is 4,5-Dichloropicolinic acid, molecular formula is C6H3Cl2NO2, 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.

A mixture of HATU (0.15 g, 0.41 mmol), 4,5-dichloropyridine-2-carboxylic acid (39 mg, 0.20 mmol) and (2S)-2-(methoxymethyl)pyrrolidine (1.32 mL, 1.02 mmol) was stirred at 25 00 for 16h. HPLC purification gave (4,5-dichloro-2-pyridyl)-[(2S)-2- (methoxymethyl)pyrrolidin-1-yl]methanone (39 mg) as a colourless oil. LCMS (Method T2) Rt= 1.39 mins, mlz 289.1 [M+H]. NMR showed two rotamers: RotamerA: 1H NMR (500 MHz, Methanol-d4) delta 8.71 (5, 1H), 7.96 (5, 1H), 4.44-4.38 (m, 1H), 3.82-3.75 (m, 1H), 3.68-3.64(m, 2H), 3.40 (5, 3H), 2.14-1.96 (m, 5H).

According to the analysis of related databases, 73455-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; LLOYD, Matthew Garth; (360 pag.)WO2018/215798; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 90145-48-5, 5-Bromopyridine-2-carboxamide, 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, Safety of 5-Bromopyridine-2-carboxamide, blongs to pyridine-derivatives compound. Safety of 5-Bromopyridine-2-carboxamide

Example 10Preparation of 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcvcloheylamino)ethyl)picolinamide(Compound-46) and 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcvclohexylamino)ethyl)picolinamide (Compound-47)[00147] 5-Bromopicolinamide 112 (1 .29 g, 6.4 mmol) and chloral (1 .25 mL) in dioxane (10 mL) were heated to 100 C. The mixture was concentrated to give 5- bromo-N-(2,2,2-trichloro-1 -hydroxyethyl)picolinamide 122 (99%).[00148] A solution of 5-bromo-N-(2,2,2-trichloro-1 -hydroxyethyl)picolinamide 122 (0.83 g, 2.39 mmol) in chloroform (20 mL) was reacted with PCI5 (0.51 g, 2.33 mmol) at 50 C for 30 minutes. The mixture was cooled to -78 C and 4- ethylcyclohexanamine was added (1 g, 7.5 mmol). After 1 hour, the mixture was warmed to room temperature. The reaction mixture was subjected to an aqueous work-up and the product extracted with chloroform. The organic solution was concentrated onto silica gel and the product was eluted (flash: 97:3 hexane:ether then prep-HPLC: Phenomenex Luna column (Si02), 10 micron, 250×50 mm, 150 mL/minute; 3:7 hexanes:dichloromethane) to give first eluting fraction: 5-bromo-N- (2,2,2-trichloro-1 -(4-ethylcyclohexylamino)ethyl)picolinamide (Compound-46, 106 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.26 (d, J = 9.9 Hz, 1 H), 8.1 1 (dd, J = 8.4, 0.6 Hz, 1 H), 8.01 (dd, J = 8.4, 2.4 Hz, 1 H), 5.56 (t, J = 9.3 Hz, 1 H), 2.96 (brs, 1 H), 1 .80-1 .71 (m, 2H), 1 .59-1 .21 (m, 10H), 0.85 (t, J = 7.2 Hz, 3H), and second eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcyclohexylamino)ethyl)picolinamide (Compound-47, 166 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.30 (d, J = 9.9 Hz, 1 H), 8.1 1 (dd, J = 8.4, 0.9 Hz, 1 H),8.01 (dd, J = 8.4, 2.1 Hz, 1 H), 5.50 (t, J = 8.7 Hz, 1 H), 2.68-2.58 (m, 1 H), 2.16-2.07 (m, 1 H), 1 .86-1 .70 (m, 4H), 1 .27-1 .01 (m, 6H), 0.96-.087 (m, 1 H) 0.83 (t, J = 7.5 Hz, 3H).

The synthetic route of 90145-48-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLERGAN, INC.; GARST, Michael E.; CHOW, Ken; HEIDELBAUGH, Todd M.; NGUYEN, Phong; WO2011/28927; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem