Category: pyridine-derivatives

Reference of 1231930-13-4, 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. 1231930-13-4, name is 3-Bromo-2-methyl-6-nitropyridine, molecular formula is C6H5BrN2O2, 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 solution of Example A6 (1.7 g, 6.40 mmol) in dioxane (30 mL) was sparged with Ar, treated with acetamide (1.512 g, 25.6 mmol), Cs2CO3 (2.085 g, 6.40 mmol), X-Phos (0.153 g, 0.320 mmol) and Pd2(dba)3 (0.293 g, 0.320 mmol) and heated at 80 C. for 20 h. The mixture was cooled to RT, treated with EtOAc, the solids removed via filtration through diatomaceous earth and rinsed well with EtOAc. The filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/DCM) to afford N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (450 mg, 24%) as a light yellow solid. MS (ESI) m/z: 289.1 (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 1231930-13-4, 3-Bromo-2-methyl-6-nitropyridine.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86521-05-3, 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 86521-05-3, name is 2-((Trimethylsilyl)ethynyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

a) 2-Ethynyl-pyridine A solution of 2-trimethylsilanylethynyl-pyridine (3.05 g, 14 mmol) in MeOH (8.5 mL) was added dropwise to potassium hydroxide solution (1 N, 14 mL) and the reaction mixture was stirred at room temperature for 1 h and then acidified with HCl (3 N, 8.5 mL) and the mixture concentrated. The residue was then diluted with water and make alkaline with solid sodium carbonate, extracted with diethyl ether and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (1.3 g, 75%) as a brown liquid. MS: m/e=176.0 [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 86521-05-3, 2-((Trimethylsilyl)ethynyl)pyridine.

Reference:
Patent; Hernandez, Maria-Clemencia; Lucas, Matthew C.; Thomas, Andrew; US2012/115844; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 117519-13-8, 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. 117519-13-8, name is 6-Chloro-2-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, 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.

Step 3: 6-Chloro-2-(trifluoromethyl)pyridine-3-sulfonyl chloride (P73c) Step (a): Thionyl chloride (42 mL) was added dropwise under ice cooling over 60 min to water (250 mL) maintaining the temperature of the mixture at 0-7C. The solution was allowed to warm to 18C and stirring was continued for 3 d. CuCI (151 mg) was added to the mixture and the resultant yellow-green solution was cooled to -3C using an acetone/ice bath. Step (b): Hydrochloric acid (36% w/w, 12.2 mL) was added with agitation to compound P73b (1.65 g, 8.4 mmol), maintaining the temperature of the mixture below 30C with ice cooling. The mixture was cooled to -5C using an ice/acetone bath and a solution of sodium nitrite (0.68 g, 9.8 mmol) in water (2.8 mL) was added dropwise over 30 min maintaining the temperature of the mixture between -5 to 0C. The resultant slurry was cooled to -2C and stirred for 10 min. Step (c): The slurry from step (b) was cooled to -5C and added to the solution obtained from step (a) over 95 min, maintaining the temperature of the mixture between -3 to 0C (the slurry from step (b) was maintained at -5C throughout the addition). As the reaction proceeded, a solid began to precipitate. When the addition was complete, the mixture was agitated at 0C for 75 min. The solid was collected by vacuum filtration, washed with ice-cooled water (2x 25 mL) and dried under vacuum at below 25C to give compound P73c (1.53 g, 66%) as yellow solid. H-NMR (CDCI3, 300 MHz) delta: 7.81 (1 H, d, J = 8.4 Hz), 8.57 (1 H, d, J = 8.4 Hz).

According to the analysis of related databases, 117519-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2013/79223; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 112110-07-3, 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.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.

General procedure: l-methyl-4-[(3-methyloxetan-3-yl)sulfamoyl]-lH-pyrrole-2-carboxylic acid (200 mg, (0182) 0.729 mmol) was dissolved in DMF (1.7 mL) and triethylamine (0.41 mL, 2.9 mmol) and HATU (360 mg, 0.95 mmol) were added. After 10 minutes 4-aminopyridine-2-carbonitrile (174 mg, 1.46 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and heated at 65C for 42 hours. The mixture was poured into water (50 mL) and the organics were extracted with ethyl acetate (3 x 40 mL). The combined organic layers were dried (Na2S04) and concentrated to dryness. The residue was purified using silica gel column chromatography (ethyl acetate in heptane from 0 to 100%) followed by prep. HPLC (Stationary phase: RP SunFire Prep C18 OBD-IotaOmicronmuiotaeta, 30 x 150mm), Mobile phase: 0.5% NH4OAc solution in water + 10% CH3CN, MeOH), resulting in compound 1 (4.6 mg). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.54 (s, 3 H), 3.94 (s, 3 H), 4.14 (d, J=6.4 Hz, 2 H), 4.60 (d, J=5.9 Hz, 2 H), 7.43 (s, 1 H), 7.66 (d, J=1.3 Hz, 1 H), 7.86 – 8.12 (m, 2 H), 8.26 (d, J=2.0 Hz, 1 H), 8.60 (d, J=5.7 Hz, 1 H), 10.68 (br. s., 1 H). Method A; Rt: 1.22 min. m/z : 374.0 (M-H)- Exact mass: 375.1. Compound 2 was prepared similarly as described for compound 1, using 5-(trifluoromethyl)-3- aminopyridine instead of 4-aminopyridine-2-carbonitrile. The reaction mixture was stirred at room temperature for 1 hour and heated at 65C for 4 hours. The mixture was poured into water (50 mL), the formed precipitate was filtered and the solids were washed with water and recrystallised from methanol/ethyl acetate (10 mL, 1 : 1). The white solids were filtered, washed with methanol (2 x 3 mL) and dried overnight in vacuum oven resulting in compound 2 (74 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.55 (s, 3 H), 3.94 (s, 3 H), 4.14 (d, J=6.2 Hz, 2 H), 4.60 (d, J=5.9 Hz, 2 H), 7.41 (s, 1 H), 7.63 (s, 1 H), 8.01 (br. s., 1 H), 8.56 (s, 1 H), 8.66 (s, 1 H), 9.13 (s, 1 H), 10.55 (br. s., 1 H). Method B; Rt: 0.84 min. m/z : 417.1 (M-H)~ Exact mass: 418.1.

Statistics shows that 112110-07-3 is playing an increasingly important role. we look forward to future research findings about 5-(Trifluoromethyl)pyridin-3-amine.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1074-98-2, 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.1074-98-2, name is 3-Methyl-4-nitropyridine 1-oxide, molecular formula is C6H6N2O3, molecular weight is 154.13, as common compound, the synthetic route is as follows.

A suspension of 3-methyl-4-nitropyridine N-oxide (2.0 g, 13 mmol) and palladium hydroxide on carbon (0.4 g) in ethanol (30 mL) was heated to 60 C. Ammonium formate (3.3 g, 52 mmol) was then added portionwise and the mixture heated at 60 C for three hours. The cool reaction mixture was filtered through Arbocel and the filtrate evaporated under reduced pressure to afford the title compound as a colourless oil, 1.81 g. LRMS (APCI+): m/z [M+H]+ 125

The chemical industry reduces the impact on the environment during synthesis 1074-98-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/121094; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1289131-55-0, 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. 1289131-55-0, name is 4-Bromo-2-(2-methoxyethoxy)pyridine, molecular formula is C8H10BrNO2, 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.

General procedure: A mixture of 4-bromo-2-ethoxypyridine (150 mg, 0.742 mmol), £>/s(pinacolato)diboron (754 mg, 2.97 mmol), PdCI2(dppf) (54.3 mg, 0.074 mmol) and potassium acetate (291 mg, 2.97 mmol) in 1 ,4- dioxane (3 ml.) was heated in a microwave at 1 10 C for 2 x 30 min. The reaction was diluted with EtOAc and filtered through a Celite column. The filtrate was evaporated to give a brown residue. This crude material was used in subsequent steps without further purification and the yield was assumed to be 100% (0.742 mmol, 185 mg).

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 1289131-55-0, 4-Bromo-2-(2-methoxyethoxy)pyridine.

Reference:
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; BAMBOROUGH, Paul; BIT, Rino, Antonio; BROWN, John, Alexander; CAMPBELL, Matthew; LINDON, Matthew, John; SHIPLEY, Tracy, Jane; THEODOULOU, Natalie, Hope; WELLAWAY, Christopher, Roland; WESTAWAY, Susan, Marie; WO2014/78257; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14916-65-5, 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 14916-65-5, name is 6-Nitropyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a so[ution of 3.50 g (11.2 mmo[) 5,10-dioxo-5H,1OH-diimidazo[1,5-a:1?,S?-d]pyrazine-1,6-dicarbony[ dich[oride (Intermediate 001) in 60 mL THF were added 3.10 g (22.4 mmo[) 6-nitropyridin-3-amine and 5.00 mL N,N-diisopropy[ethy[amine. The resu[ting mixture was stirred for 1 hour at room temperature under an argon atmosphere.

According to the analysis of related databases, 14916-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERSTAFF, Jens; WAGNER, Sarah; BASTING, Daniel; GOLZ, Stefan; BENDER, Eckhard; LI, Volkhart Min-Jian; LIENAU, Philip; LIU, Ningshu; SIEGEL, Franziska; BAUSER, Marcus; SUeLZLE, Detlev; HOLTON, Simon; BAIRLEIN, Michaela; BUCHGRABER, Philipp; BALINT, Jozsef; WO2015/150449; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 898746-42-4, name is 6-Fluoro-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C7H5FN2

Preparation 1Synthesis of 6-fluoro-l -methyl- lH-pyrrolo[2,3-b]pyridine.Jf)3 C H3 To a solution of 6-fluoro-lH-pyrrolo[2,3-b]pyridine (250 g, 1.84 mol) in dimethylformamide (2.50 L) is added potassium carbonate (507.6 g; 3.67 mol), followed by methyl iodide (171.6 mL, 2.75 mol). The reaction is stirred at room temperature overnight. The reaction mixture is poured into water (3000 mL) and extracted with Et20(3 x 1500 mL). The organic extracts are combined and washed with water (4 x 1000 mL), then brine, and dried over Na2S04. The solvent is evaporated to give a light brown oil which, on standing, gives clear colorless crystals, with a little mobile liquid on top of the crystals. The liquid is decanted off and discarded to leave the product as a crystalline solid (257.3 g, 1.71 moles). XH-NMR (400MHz, CDC13): delta 7.93 (t, 1H), 7.11 (d, 1H), 6.69 (d, 1H), 6.46 (d, 1H), 3.83 (s, 3H).

The synthetic route of 898746-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; LAMAS-PETEIRA, Carlos; RICHARDS, Simon, James; SAPMAZ, Selma; WALTER, Magnus, Wilhelm; WO2012/74769; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 936841-69-9, 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 936841-69-9, name is 4-(Trifluoromethyl)picolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-(trifluoromethyl)pyridine-2-carbonitrile (500 mg, 3.0 mmol) in 10 ml ethanol was added hydroxylammonium chloride (302 mg, 4.0 mmol) and triethylamine (382 mg, 4.0 mmol) and then the reaction mixture was stirred 13 h at 50 C. After cooling to RT, the solvent was evaporated and the crude was solved in dichloromethane and extracted with water. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (432 mg, 65 % of theory, 90 % purity). The compound was used without further purification. LC-MS (method 2B): RT = 1.78 min, m/z = 206 (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 936841-69-9, 4-(Trifluoromethyl)picolinonitrile.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3430-26-0, 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.3430-26-0, name is 2,5-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, molecular weight is 250.92, as common compound, the synthetic route is as follows.

To a solution of 2,5-dibromo-4-methylpyridine (20.00 g, 80.00 mmol) in acetonitrile (350 mL) was added sodium iodide (24.00 g, 160.0 mmol) and acetyl chloride (4.70 g, 59.9 mmol) at 0C under N2 in a 500 mL round bottom flask. The mixture was heated to 90C and stirred for 16 h. LC-MS showed the reaction was complete. The mixture was filtered, the precipitate was dissolved with DCM (50 mL) and water (50 mL), the organic layer was washed with water (30 mL x 2), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound, which was used directly for next step without further purification.1H NMR (CDCl3, 400 MHz): 8.39 (s, 1H), 7.60 (s, 1H), 2.33 (s, 3H). MS (ESI) m/z 297.8/299.8 (M+H).

The chemical industry reduces the impact on the environment during synthesis 3430-26-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; KUANG, Rongze; KUMAR, Puneet; DUFFY, Joseph, L.; ZHU, Cheng; ALI, Amjad; YANG, Meng; DEBENHAM, John, S.; (124 pag.)WO2018/39094; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem