Pyridine-derivatives

Application of 944401-65-4, 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.944401-65-4, name is 5-Bromo-6-fluoropyridin-2-amine, molecular formula is C5H4BrFN2, molecular weight is 191, as common compound, the synthetic route is as follows.

Synthesis of 5-cyclopropyl-6-fluoropyridin-2-amine. A solution of 5-bromo-6-fluoropyridin-2-amine (3.0 g, 15.8 mmol), cyclopropylboronic acid (2.04 mg, 23.7 mmol), Pd(OAc)2 (354 mg, 1.58 mmol), PCy3 (886.2 mg, 3.16 mmol) and K3PO4(6.7 g, 31.6 mmol) in dioxane/H2O (30 mL/3 mL) was stirred at 100 C. for 16 h. Then the reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (100 mL*3). The combined organic layers were dried over Na2SO4 and concentrated to give the desired compound 5-cyclopropyl-6-fluoropyridin-2-amine (yellow oil, 2.2 g). ESI-MS [M+H]+: 153.2.

Statistics shows that 944401-65-4 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-6-fluoropyridin-2-amine.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19524-06-2, 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 19524-06-2, name is 4-Bromopyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

CuI (95 mg, 0.50 mmol), (Ph3P)2PdCl2 3(174 mg, 0.25 mmol), Na ascorbate (98 mg, 0.50 mmol) and 4-bromopyridinehydrochloride 22 (970 mg, 5.0 mmol) wereplaced in a flask, which was degassed and filled with Ar. Pri2NH (10 mL) andTHF (10 mL) were added. The mixture was stirred at 40°C for 30 min. Me3SiC?CH (532 mg, 5.0 mmol) was added and themixture was stirred at 40°C for 10 h. Evaporation and chromatography (petroleumether / EtOAc 5:1 ? 3:1) gave 20l (767mg, 89percent) as a pale buff oil (lit.7 yellow liquid); 1H NMR(CDCl3) d 0.27 (9 H, s, SiMe3), 7.29 (2 H, d, J = 4.4 Hz, 3,5-H2) 8.55 (2 H, d, J = 4.4 Hz, 2,6-H2); 13C NMR (CDCl3)d -0.002 (SiMe3),100.24 (ethyne 2-C), 102.31 (ethyne 1-C), 126.16 (3,5-C2), 131.52(4-C), 150.03 (2,6-C2).

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 19524-06-2, 4-Bromopyridine hydrochloride.

Reference:
Article; Kumpan, Katerina; Nathubhai, Amit; Zhang, Chenlu; Wood, Pauline J.; Lloyd, Matthew D.; Thompson, Andrew S.; Haikarainen, Teemu; Lehtioe, Lari; Threadgill, Michael D.; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3013 – 3032;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55304-90-0, Adding some certain compound to certain chemical reactions, such as: 55304-90-0, name is (2,6-Dichloropyridin-3-yl)methanol,molecular formula is C6H5Cl2NO, 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 55304-90-0.

180 g (1.01 mols) of 2,6-dichloro-3-hydroxymethylpyridine are then heated under reflux for 2 hours with 600 g (6.9 mols) of manganese dioxide in 4 l of benzene. The reaction mixture is filtered while still hot and the benzene is evaporated. After drying the residue in a vacuum drying cabinet, 2,6-dichloropyridine-3-aldehyde is obtained.

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. 55304-90-0, (2,6-Dichloropyridin-3-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ciba-Geigy Corporation; US3974166; (1976); A;,
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 159307-02-5, name is 6-Acetylpicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H6N2O

Step c. To a solution of 6-acetylpicolinonitrile (0.1 g, 0.68 mmol) in acetic acid (10 ml) was added bromine (0.108 g, 0.68 mmol) in glacial acetic acid (5 ml) drop wise at 15C. The reaction mixture was stirred at rt for 20 h. The resulting reaction mixture was poured into saturated NaHC03 solution (30 ml) and neutralized with slow addition of solid Na2C03. The obtained mixture was extracted with EtOAc (3 x 40 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure yielding 6-(2-bromoacetyl)picolinonitrile (0.4 g, 1.77 mmol). MS: ES+ 224.7; 226.7.

With the rapid development of chemical substances, we look forward to future research findings about 159307-02-5.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; KEMP, Mark; STOCKLEY, Martin; JONES, Alison; (138 pag.)WO2017/9650; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13362-26-0 , The common heterocyclic compound, 13362-26-0, name is Ethyl 2-aminonicotinate, molecular formula is C8H10N2O2, 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.

Example 125 Synthesis of ethyl 2-amino-5-bromonicotinate. To a solution of ethyl 2-aminonicotinate (25 g, 150.44 mmol) in CH3CN (500 mL) was added NBS (32.1 g, 180.5 mmol) in portions over 30 min at 0 C. The mixture was warmed to RT and stirred for 2 h. The reaction mixture was concentrated. The residue was washed with NaHCO3 aqueous (300 mL) and extracted with EtOAc (300 mL*3), the combined organic layers were concentrated to give ethyl 2-amino-5-bromonicotinate (36.9 g, yield: 100%) as a yellow solid, which was used in the next step without further purification. ESI-MS [M+H]+: 245.1.

The synthetic route of 13362-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 100704-10-7, Adding some certain compound to certain chemical reactions, such as: 100704-10-7, name is (2-Chloropyridin-4-yl)methanol,molecular formula is C6H6ClNO, 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 100704-10-7.

A sample of (2-chloropyridin-4-yl)methanol (110.0 mg, 0.77 mmol) was dissolved in anhydrous THF (1.5 mL), treated with /Y,iV-diisopropylethylamine (0.29 mL, 1.69 mmol) and cooled to -78 0C. Methanesulfonyl chloride was added (0.07 mL, 0.84 mmol), and the reaction mixture was allowed to slowly warm to room temperature overnight. The reaction mixture was then diluted with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo yielding the title compound (110.0 mg, 88.6%).1H NMR (300 MHz, CD3CN) delta 8.40 (d, 1 H), 7.49 (s, 1 H), 7.39 (d, 1 H) and 4.63 ppm (s, 2 H); ES-MS m/z 183.2 [M+Na]+, HPLC RT (min) 2.30.

According to the analysis of related databases, 100704-10-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/96338; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 552331-00-7, 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 552331-00-7 as follows.

Step 1: A 20 mL reaction vessel was charged with 4-iodopyridin-2-amine (1.5 g, 6.8 mmol) and 1H-pyrazole(4.0 g, 58.9 mmol). Concentrated hydrochloric acid (1.5 ml) and 1,4-dioxane (1.5 mL) were added, and the reactionvessel was sealed. The mixture was irradiated in a microwave oven at 120 C for 45 min and then at 130 C for 60 min.The mixture was cooled to rt and then diethyl ether (6 ml) and ethanol (3 ml) were added. The mixture was sonicatedfor 10 min, and the solid was collected by filtration and washed with diethyl ether and n-hexane to give 4-(1H-pyrazol-1-yl)pyridin-2-amine hydrochloride (1.2 g, 90%) as a white solid. LCMS (ESI) m/z 161 (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,552331-00-7, its application will become more common.

Reference:
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59782-85-3, 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. 59782-85-3, name is 2,5-Dichloronicotinic 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.

To a stirred solution of 2,5-dichloronicotinic acid (Syn. Commun. 1989, 19, 553-9, 2.0 g, 10.4 mmol) and methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride (step 3 of Example 8, 2.35 g, 10.9 mmol) in dichloromethane (10 mL) was added 1,1′-carbonyldiimidazole (CDI) (1.77 g, 10.9 mmol) in small portions. After being stirred overnight, the reaction mixture was poured into water (80 mL). The precipitated solids were collected by the filtration and dried. The crude product was purified by flush column chromatography on silica gel (100 g) eluding with dichloromethane/ethyl acetate (20/1) to afford 3.4 g (93%) of the title compound as white solids: 1H-NMR (CDCl3) delta 8.42 (1H, d, J=2.6 Hz), 8.10 (1H, d, J=2.6 Hz), 8.04 (2H, d, J=8.6 Hz), 7.46 (2H, d, J=8.6 Hz), 6.82 (1H, d, J=7.3 Hz), 5.40-5.30 (1H, m), 3.92 (3H, s), 1.64 (3H, d, J=7.0 Hz); MS (ESI) m/z 353 (M+H)+, 351 (M-H)-.

According to the analysis of related databases, 59782-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2005/250818; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 113770-88-0, 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. 113770-88-0, name is 3-Fluoro-4-cyanopyridine, molecular formula is C6H3FN2, 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.

3-Fluoro-isonicotinonitrile (0.50 g, 4.10 mmol) was dissolved in ethanol (8 mL) and treated with hydrazine hydrate (0.31 g, 6.1 mmol). After stirring at 70 C for 16 h, the mixture was cooled to RT and concentrated in vacuo and dried to yield the title compound (0.66 g, 100% of theory). LC-MS (Method 2B): Rt = 0.51 min, MS (ESIPos): m/z = 135 [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 113770-88-0, 3-Fluoro-4-cyanopyridine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; CANCHO-GRANDE, Yolanda; BEYER, Kristin; ROeHRIG, Susanne; KOeLLNBERGER, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; WO2015/67549; (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. 126325-47-1, name is 6-Bromo-2-methylpyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Intermediate 4: 6-Methanesulfonyl-2-methyl-pyridin-3-ylamine; A mixture of 3-amino-6-bromo-2-methylpyridine (ECA International Corporation, Palatine, Ill., USA; 2.0 g, 10.7 mmol), sodium methanesulfinate (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 5.13 g, 42.8 mmol), copper trifluoromethanesulfonate benzene complex (598 mg, 1.07 mmol), and N,N’-dimethylethylenediamine (115 muL, 1.07 mmol) in dimethylsulfoxide (15 mL) was heated at 150 C. for 4 h. The mixture was cooled and water and ethyl acetate were added. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed twice with water, and then concentrated to approximately 5 mL. This gave a precipitate which was filtered off, washed with a small amount of ethyl acetate and air dried to give 6-Methanesulfonyl-2-methyl-pyridin-3-ylamine (1 g, 50%) as a brown powder. 1H NMR (300 MHz, DMSO-d6) delta 2.30 (s, 3H), 3.05 (s, 3H), 6.04 (br s, 2H), 6.98 (d, 1H, J=8.4 Hz), 7.55 (d, 1H, J=8.2 Hz).

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, 126325-47-1, 6-Bromo-2-methylpyridin-3-amine.

Reference:
Patent; Erickson, Shawn David; Gillespie, Paul; Guertin, Kevin Richard; Karnachi, Prabha Saba; Kim, Kyungjin; Ma, Chun; McComas, Warren William; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Tilley, Jefferson Wright; Zhang, Qiang; US2009/286812; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem