Day: February 25, 2021

Reference of 59786-31-1, 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. 59786-31-1, name is Methyl 3-bromoisonicotinate, molecular formula is C7H6BrNO2, 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.

Compound 43a. To a solution of ethyl 3-bromoisonicotinate (0.4 g, 1.85 mmol, 1.0 equiv) in toluene (20 mL) was added 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.58 g, 2.77 mmol, 1.5 equiv), K2CO3 (0.51 g, 3.78 mmol, 2.0 equiv) and resulting reaction mixture purged with N2 gas for 10 min. followed by the addition of Pd(PPh3)4 (0.065 g, 0.093 mmol. 0.05 equiv). The resulting reaction mixture was heated at 100 C. for overnight. Product formation was confirmed by LCMS. After the completion of reaction, the reaction mixture was filtered through Celite bed, washed with ethyl acetate (100 mL). Filtrate was concentrated under reduced pressure. The crude product obtained was purified by flash chromatography (0-10% ethyl acetate in hexane as an eluent) to obtain methyl 3-(cyclohex-1-en-1-yl)isonicotinate (0.170 g, 42.4%) as colorless oil. (0763) LCMS 218.2 [M+H]+ (0764) 1H NMR (400 MHz, DMSO-d6) delta 8.60 (d, J=5.3 Hz, 1H), 8.52 (s, 1H), 7.56 (d, J=5.3 Hz, 1H), 5.62 (br. s., 1H), 2.24-2.06 (m, 4H), 1.77-1.54 (m, 4H).

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 59786-31-1, Methyl 3-bromoisonicotinate.

Reference:
Patent; Praxis Biotech LLC; ALFARO, Jennifer; BELMAR, Sebastian; BERNALES, Sebastian; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; US2019/185451; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 571189-16-7, 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. 571189-16-7, name is tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

Example 101h tert-Butyl 4-(6-Aminopyridin-3-yl)piperazine-1-carboxylate 101h A 500-mL bottle was purged with nitrogen and charged with tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate 101g (3.1 g, 10 mmol), 10% palladium on carbon (50% wet, 1.0 g) and ethanol (100 mL). It was evacuated, charged with hydrogen gas, and stirred for 16 h at room temperature. The hydrogen was then evacuated and nitrogen was charged into the bottle. The catalyst was removed by filtration through a pad of CELITE and the filtrate concentrated under reduced pressure to afford 101h (2.7 g, 97%). MS: [M+H]+ 279

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,571189-16-7, its application will become more common.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 39856-50-3, 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 39856-50-3, name is 5-Bromo-2-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Into a solution of 5-bromo-2-nitropyridine (30 g, 148 mmol) in DMSO (1 L) were added K2CO3 (40 g, 296 mmol) and teri-butyl piperazine-l-carboxylate (28g, 148 mmol). The mixture was stirred at 65 degree for overnight. After cooling down, it was poured into water (2 L). The solid precipitated was collected and dried under vacuum. It was then further purified by flash column eluting with 20:1 petroleum ether/ethyl acetate and then with methylene chloride to give 188a as a yellow solid (17 g, 37%). MS: [M+H]+ 309.

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 39856-50-3, 5-Bromo-2-nitropyridine.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); 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.2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, molecular weight is 111.1169, as common compound, the synthetic route is as follows.name: 2-Fluoro-5-methylpyridine

Diisopropylamine (910.7 mg, 1.261 mL, 9.000 mmol) was dissolved in dry TetaF(20mL) and cooled to -78 0C, n-Buli (3.600 mL of 2.5 M, 9.000 mmol) was added slowly dropwise and the resultant mixture was then allowed to warm to -20 0C over 40min before being cooled back down to -78 0C.[ 00363 ] A solution of 2-fluoro-5-methyl-pyridine (1.0 g, 9.000 mmol) in dry THF(1OmL) was added dropwise and the solution was stirred at this temp for 2 hours. A solution of iodine (2.284 g, 463.3 muL, 9.000 mmol) in THF (1OmL) was then added and the resultant mixture stirred for a further 1 hour at this temp before being quenched with water. The resulting mixture was partitioned between sodium thiosulfate solution and Et2theta, organics separated and washed further with saturated NaCl. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a colourless oil. The resulting mixture was purified by column chromatography (30% EtOAc in hexanes, ~200mL silica) to give a colourless foam (1.409g, 66% Yield). 1 H NMR (400.0 MHz, DMSO) d 1 .42 (s, 1 H) and 7.07 – 7.12 (s, 2H) ppm

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2369-19-9, 2-Fluoro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/73300; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, 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, Recommanded Product: 64951-08-2, blongs to pyridine-derivatives compound. Recommanded Product: 64951-08-2

Working Example 47 To a mixture of 3-methoxymethyl-1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (500 mg) obtained in Reference Example 14, imidazo[1,2-a]pyridine-2-carboxylic acid (211 mg), triethylamine (657 mg) and N,N-dimethylformamide (3 ml) is added dropwise under ice-cooling, while stirring, a solution of diethyl cyanophosphonate (277 mg) in N,N-dimethylformamide (1 ml), and the mixture is stirred for one hour. The reaction mixture is poured into ice-water and extracted with ethyl acetate. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is purified by means of a silica gel column chromatography (eluent: ethyl acetate), followed by recrystallization to give 2-[2-methoxymethyl-4-(3,4,5-trimethoxybenzyl)piperazin-1-ylcarbonyl]imidazo[1,2-a]-pyridine as colorless prisms (354 mg), m.p. 129-130C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP368670; (1990); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88511-27-7, 4-Amino-3-iodopyridine, 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 4-Amino-3-iodopyridine, blongs to pyridine-derivatives compound. Safety of 4-Amino-3-iodopyridine

Example 3; 8-Eth l-6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indoleSi(OEt) (284 mg, 1 .36 mmol) was added to a solution of 4-amino-3-iodopyridine (300 mg, 1 .36 mmol), 4-ethylcyclohexanone (344 mg, 2.72 mmol) and PPTS (68 mg, 0.27 mmol) in pyridine (3 ml). The mixture was flushed with N2 and heated at 160C under microwave for 45 min. Pd(PPh3) (78 mg, 0.068 mmol) and dicyclohexylmethylamine (319 mg, 1 .63 mmol) were added to the reaction mixture. The mixture was flushed with N2, then heated at 170C under microwave for 2 hours. The reaction mixture was cooled and partitioned between H2O and EtOAc. The organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was subjected to chromatography (silica gel treated with Et3N in DCM, eluting with MeOH in DCM) to afford 220 mg of impure product, which was purified again with HPLC (Ci8, eluting with 10-100% CH3CN in H2O with 0.1 % TFA). 142 mg of gel was obtained from pure fractions. The gel was treated with MeOH and concentrated to give the title compound as a white crystalline solid (142 mg, TFA salt, 33%, hygroscopic).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88511-27-7, 4-Amino-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI; GROSS, Alexandre; LI, Ronghua; MAJID, Tahir Nadeem; MOORCROFT, Neil David; YU, Kin T.; ZILBERSTEIN, Asher; WO2011/84439; (2011); 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. 7379-35-3, name is 4-Chloropyridine hydrochloride. A new synthetic method of this compound is introduced below., Computed Properties of C5H5Cl2N

Step 1. Methyl(4-nitrophenyl)-4-pyridylamine To a suspension of N-methyl-4-nitroaniline (2.0 g, 13.2 nmmol) and K2CO3 (7.2 g, 52.2 mmol) in DMPU (30mL) was added 4-chloropyridine hydrochloride (2.36 g, 15.77 mmol). The reaction mixture was heated at 90¡ã C. for 20 h, then cooled to room temperature. The resulting mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL). The organic layer was washed with water (100 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, gradient from 80percent EtOAc/20percent hexanes to 100percent EtOAc) to afford methyl(4-nitrophenyl)-4-pyridylamine (0.42 g)

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, 7379-35-3, 4-Chloropyridine hydrochloride.

Reference:
Patent; BAYER CORPORATION; US2004/102636; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13269-19-7, 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. 13269-19-7, name is 2-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

General procedure: choloro acetylcholoride (24mmol) and Et3N (24mmol) was added to a solution of 2-chloro-3-aminopyridine 7e (20mmol) in CH2Cl2 (20mL) at room temperature. The mixture was stirred for 5 hrs, and the solvent was evaporated under vacuum. The residue was purified by column chromatography (CH2Cl2:CH3OH: 30:1) on silica gel to obtain pure compound 8e as a white powder in 72% yield. To a solution of amide derivative 8e (5mmol) and potassium carbonate (7.5mmol) in acetonitrile (20ml) was added isothiocyanate (6mmol) during about 5min. The reaction mixture was stirred at room temperature overnight, and the solvent was evaporated under vacuum. The residue was extracted with ethyl acetate (20mL¡Á3). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The obtained residue was purified by silica gel flash chromatography column (CH2Cl2:CH3OH: 30:1) to afford 5l as a white solid in 82% yield. To a solution of 5l (1mmol) in glacial acetic acid (5mL) were added aldehyde 6b (1mmol) and beta-alanine (1mmol). The resulting mixture was stirred under reflux for 2h. Upon completion of the reaction, the mixture was cooled, the reaction was quenched with water, and the precipitate was filtered off, then the residue was purified by column chromatography (CH2Cl2:CH3OH: 15:1) on silica gel to obtain pure compound 2r as a faint yellow powder in 80% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13269-19-7, its application will become more common.

Reference:
Article; Cai, Ming-Guang; Wu, Yang; Chang, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2517 – 2520;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1452-63-7 , The common heterocyclic compound, 1452-63-7, name is Picolinohydrazide, molecular formula is C6H7N3O, 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) Pyridine-2-carboxylic acid (1-amino-2-benzenesulfonyl-ethylidene)-hydrazide A suspension of 9.24 g (0.035 mol) 2-(phenylsulfonyl)-ethanimidic acid ethyl ester hydrochloride in 100 ml chloroform was treated with 35 ml 1N aqueous sodium hydoxide. 14 ml of a saturated aqueous sodiumbicarbonate solution was added and the mixture was extracted with chloroform. The extracts were combined and dried with sodium sulfate and the solvents were distilled off under reduced pressure. The resulting colorless oil was stirred together with 5.12 g (0.037 mol) 2-picolinyl hydrazide in 60 ml chloroform for 24 hours at 50 C. The resulting precipitate was filtered off and dried. A quantitative yield of pyridine-2-carboxylic acid (1-amino-2-benzenesulfonyl-ethylidene)-hydrazide was obtained as white crystals. MS m/e (%): 319 (M+H+, 100).

The synthetic route of 1452-63-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US6355653; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 38222-83-2, Adding some certain compound to certain chemical reactions, such as: 38222-83-2, name is 2,6-Di-Tert-butyl-4-methylpyridine,molecular formula is C14H23N, 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 38222-83-2.

4-Bromomethyl-2,6-di-t-butylpyridine (Compound A3) To a mixture of 2,6-di-t-butyl-4-methylpyridine (Aldrich, 2.0 g, 9.73 mmol) in 25 ml of dry CCl4 was added benzoyl peroxide (24 mg, 0.097 mmol) and NBS (1.9 g, 10.7 mmol). The reaction mixture was refluxed for 16 hours. After it cooled to room temperature, the solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, hexane) to give an oil (1.957 g) which contained 82% of the desired product and 18% of the starting material. 1 H NMR delta 7.09 (s, 2H), 4.39 (s, 2H), 1.35 (s, 18H).

According to the analysis of related databases, 38222-83-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan Sales, Inc.; US5965606; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem