Pyridine-derivatives

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.58584-63-7, name is (6-Methoxypyridin-3-yl)methanol, molecular formula is C7H9NO2, molecular weight is 139.15, as common compound, the synthetic route is as follows.Quality Control of (6-Methoxypyridin-3-yl)methanol

To a stirred solution of (6-methoxypyridin-3-yl)methanol (49.8 mg, 0.358 mmol) in DMF (0.5 ml.) at 0 C was added sodium hydride (60% dispersion in mineral oil) (10.73 mg, 0.447 mmol) and the reaction mixture stirred for 15 min prior to the addition of 4- methylbenzene-l-sulfonyl chloride (85 mg, 0.447 mmol). The reaction was stirred for a further 30 min at this temperature. In a separate flask, 5-(4-chloro-lH-imidazol-2-yl)-l,3- dimethylpyridin-2(lH)-one (for an example preparation, see Intermediate 12, 40 mg, 0.179 mmol) was dissolved in DMF (0.5 ml.) at 0 C, to which sodium hydride (60% dispersion in mineral oil) (8.58 mg, 0.358 mmol) was added and the reaction stirred for a further 30 min. The solution containing the tosylated pyridine was added dropwise to the flask containing the imidazole, and the reaction stirred for a further 16 h. The solvent was removed in vacuo and the crude product was purified by MDAP (Method A) to afford the title compound as a colourless film (16 mg, 0.04 mmol, 23%). LCMS (System A): tRET = 0.79 min; MH+ 345.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-63-7, (6-Methoxypyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAXTER, Andrew; BIT, Rino, Antonio; BROWN, John, Alexander; HIRST, David; HUMPHREYS, Philip; JONES, Katherine, Louise; PATEL, Vipulkumar, Kantibhai; (124 pag.)WO2018/41964; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 882521-63-3, 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. 882521-63-3, name is 7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine. A new synthetic method of this compound is introduced below.

General procedure: To a microwave tube was added [1,2,4]triazolo[1,5-a]pyridin-2-amine 13 (1 equiv), K2CO3 (2.0 equiv), Pd(PPh3)4 (0.056 equiv), and the corresponding boronic acid (1.5 equiv). 5 mL of EtOH:H2O (1:1) was used as solvent, and the microwave conditions employed were 150 C for 30 min. After solvent evaporation, the product was purified by flash chromatography on silica gel using as eluent a gradient of EtOAC (0 – 100%) in n-hexane or MeOH (0 – 10%) in DCM to afford the desired compound 16 (adapted from 4).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,882521-63-3, 7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Ribeiro, Carlos J.A.; Kankanala, Jayakanth; Xie, Jiashu; Williams, Jessica; Aihara, Hideki; Wang, Zhengqiang; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 257 – 261;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139022-25-6, 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. 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, 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.

(5-((3-bromophenoxy)methyl)-4,5-dihydroisoxazol-3-yl)methanamine hydrochloride (±) (0.300 g, 0.932 mmol) was reacted with imidazo[l,2-a]pyridine-6-carboxylic acid (0.181 g, 1.119 mmol) in the presence of BOP reagent (0.452 g, 1.025 mmol) and Nu,Nu- diisopropylethylamine (0.359 g, 2.790 mmol) in Nu,Nu-dimethylformamide (10 mL) at room temperature for 16 h. The reaction mixture was diluted with water (10 mL) extracted with ethyl acetate (50 mL) and washed with water (4 x 50 mL). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (methanol/dichloromethane = 2/98) to give titled compound (0.250 g, 62 %) as a solid. LCMS: m/z 429.3 [M+H] +; lU NMR (300 MHz, Chloroform-d) delta 8.83 (m, 1H), 7.73 – 7.62 (m, 3H), 7.44 (dd, / = 9.4, 1.8 Hz, 1H), 7.15 – 7.04 (m, 2H), 6.90 – 6.79 (m, 2H), 5.07 – 4.98 (m, 1H), 4.43 (d, / = 5.3 Hz, 2H), 4.06 (d, / = 4.7 Hz, 2H), 3.25 (dd, / = 17.3, 10.7 Hz, 1H), 3.09 (dd, / = 17.3, 7.2 Hz, 1H).

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 139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 845306-08-3, 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.845306-08-3, name is tert-Butyl 5-bromopicolinate, molecular formula is C10H12BrNO2, molecular weight is 258.11, as common compound, the synthetic route is as follows.

A 20 mL sealed tube was charged with tris(dibenzylideneacetone)dipalladium(0) (0.049 g, 0.053 mmol), tri-teri-butylphosphonium tetrafluoroborate (Strem, 0.037 g, 0.127 mmol), tert- butyl 5-bromopicolinate (Combi-Blocks, 0.456 g, 1.767 mmol), and N,N-dimethylformamide (8.8 mL). The tube was purged with a nitrogen stream for 2 minutes, sealed and stirred at ambient temperature. 2-cyanoethylzinc bromide (0.5 M in tetrahydrofuran, 4.77 mL) was added dropwise over 2 minutes via a cannula needle. The reaction mixture was stirred at ambient temperature for 6 hours and then at 75 C for 18 hours. The reaction was cooled to ambient temperature and quenched with water (0.5 mL), and the resulting mixture was concentrated under reduced pressure briefly to remove most of the tetrahydrofuran solvent. The resulting solution was filtered through a glass microfiber frit and directly purified by reverse -phase flash chromatography [150 g Redisep Gold C18 column, flow rate 110 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid)] to give the title compound (0.15 g, 0.65 mmol, 37% yield). MS (ESI+) m/z 233 (M+H)+.

Statistics shows that 845306-08-3 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 5-bromopicolinate.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3939-13-7, 2-Fluoronicotinonitrile, 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, Computed Properties of C6H3FN2, blongs to pyridine-derivatives compound. Computed Properties of C6H3FN2

Synthesis of intermediate VX001: Isoxazolo[5,4-b]pyridin-3-amine 909 mg (8.1 mmol) of KO-t-Bu were added, with vigorous stirring, to a suspension of 668 mg (8.9 mmol) of acethydroxamic acid in DMF (20 ml), and the mixture was stirred for 30 min at RT. 990 mg (8.1 mmol) of 2-fluoro-nicotinonitrile were then added, and stirring was carried out for a further 5 h at 50 C. The mixture was then extracted with EA and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 7:3) of the residue yielded 305 mg (2.3 mmol, 28%) of isoxazolo[5,4-b]pyridin-3-amine.

The synthetic route of 3939-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUNENTHAL GMBH; US2010/234419; (2010); 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. 42753-71-9, name is 2-Amino-5-bromo-6-methylpyridine. A new synthetic method of this compound is introduced below., Computed Properties of C6H7BrN2

Example A3 A 0 C. solution of sulfuric acid (125 mL) was treated drop-wise with H2O2(30%, 63.1 mL, 2058 mmol), stirred for 15 min, treated drop-wise with a cold solution of 6-amino-3-bromo-2-picoline (35 g, 187 mmol) in sulfuric acid (125 mL), allowed to warm to RT and stirred for 4 h. The mixture was poured onto ice (1.2 kg) and the resulting solid collected via filtration, dissolved in DCM, washed with brine, dried over Na2SO4 and concentrated to dryness. The aqueous filtrate and washes were combined, extracted with DCM (2*) and the combined organics were dried over Na2SO4, concentrated to dryness, purified via silica gel chromatography (EtOAc/Hex) and combined with the above-isolated solid to afford 3-bromo-2-methyl-6-nitropyridine (25.59 g, 63%). MS (ESI) m/z: 218.9 (M+H+).

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, 42753-71-9, 2-Amino-5-bromo-6-methylpyridine.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); 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. 180748-30-5, name is (4-Chloropyridin-2-yl)methanamine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 180748-30-5

[0411] To (4-chloro-2-pyridyl)methanamine (59, 0.51 g, 3.58 mmol) in dichloromethane (50 mL) was added l-isothiocyanato-4-nitro-benzene (65, 0.66 g, 3.65 mmol). The reaction mixture was stirred at room temperature for about 1 hour. LCMS showed the reaction was complete. The reaction was concentrated, and washed with ethyl acetate and hexane to give product (63).

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, 180748-30-5, (4-Chloropyridin-2-yl)methanamine.

Reference:
Patent; PLEXXIKON INC.; ZHANG, Jiazhong; POWERS, Hannah; ALBERS, Aaron; PHAM, Phuongly; WU, Guoxian; BUELL, John; SPEVAK, Wayne; GUO, Zuojun; WALLESHAUSER, Jack; ZHANG, Ying; (229 pag.)WO2019/183145; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-77-5, 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. 1620-77-5, name is 5-Methylpicolinonitrile. A new synthetic method of this compound is introduced below.

Synthesis Example 1 Ethyl 5-methylpyridine-2-carboxylate STR24 200 ml of ethanol and 100 ml (1.88 mol) of concentrated sulfuric acid were added to 55.5 g of 5-methylpyridine-2-carbonitrile to form a homogeneous solution, followed by heating under reflux for 2 days. The reaction liquid was gradually poured into a saturated aqueous solution of sodium hydrogencarbonate under cooling with ice to neutralize the sulfuric acid, followed by extraction with dichloromethane. The organic layer was washed with a saturated aqueous solution of common salt and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in a reduced pressure to give 78.1 g of a brown oil of the title compound as the crude product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1620-77-5, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US5789403; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1628-89-3, Adding some certain compound to certain chemical reactions, such as: 1628-89-3, name is 2-Methoxypyridine,molecular formula is C6H7NO, 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 1628-89-3.

A: 2 mol of 6-methoxypyridine and 700 ml of a 22percent potassium chloride solution were added to the reaction vessel.1.2L mass fraction of 26percent heptane solution, control solution temperature to 15 ° C,Adding an aqueous solution, 6 mol of aluminum isopropoxide, controlling the stirring speed of 370 rpm, and continuing the reaction for 120 min; B: Then, 6 mol of antimony trichloride powder was added, the temperature was controlled at 26 ° C, the reaction was continued for 3 h, then the temperature was lowered to 8 ° C, allowed to stand for 50 min, and the solution was layered.The oil layer was separated and washed 5 times with a 15percent sodium sulfate solution.The solution was washed 8 times with a mass fraction of 77percent in xylene and recrystallized from a cyclohexene solution having a mass fraction of 86percent.The dehydrating agent was dehydrated with anhydrous sodium sulfate to obtain 216.038 g of the obtained N-methylpyridin-2-one, and the yield was 99.1percent.

According to the analysis of related databases, 1628-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Kadifu Technology Co., Ltd.; Liao Runai; (4 pag.)CN108239022; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1188477-11-3, 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. 1188477-11-3, name is tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate. A new synthetic method of this compound is introduced below.

To a mixture of tert-butyl ((5-bromopyridin-2-yl)methyl)carbamate (2.2 g, 7.7 mmol) in 1,4-dioxone (4 mL) was added a solution of HCl in 1,4-dioxane (20 mL, 60 mmol, 3 M HCl in 1,4-dioxane). The mixture was stirred at 28C for 2 hr then concentrated to dryness to give the crude product (2.2 g crude) as yellow solid which was directly used in the next step without further purification. LC-MS: m/z 186,188 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1188477-11-3, tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; SPERO THERAPEUTICS, INC.; ZAHLER, Robert; (262 pag.)WO2016/112088; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem