Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, 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, Quality Control of N-(4-Bromopyridin-2-yl)acetamide, blongs to pyridine-derivatives compound. Quality Control of N-(4-Bromopyridin-2-yl)acetamide

1001161 To a mixture of N-(4-bromopyridin-2-yl)acetamide (17.2 g, 80 mmol), 4,4,4,4,5,5,5,5- octamethyl-2,2-bi-1,3,2-dioxaborolane (26.4 g, 104 mmol), Pd(dppf)C12 (11.7 g, 16 mmol) and KOAc (23.6 g, 240 mmol) under an atmosphere of nitrogen was added anhydrous DMF (1500 mL). The mixture was allowed to stir at 80 C for 3.5 h. The solvent was removed and the residue was diluted with EtOAc (1000 mL). Activated carbon (100 g) was added. The slurry was heated at reflux for 5 mm and then filtered. The organic solution was concentrated and the residue was recrystallized from EtOAc to give N[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (6.1 g, 29%) as a white solid. ?H NMR (400 MHz, DMSO-d6): 1.29 (s, 12H), 2.09 (s, 3H), 7.24 (dd, J= 6.0, 1.2 Hz, 1H), 8.30-8.33 (m, 2H), 10.47 (br s, 1H).

The synthetic route of 1026796-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; XU, He; YE, Yingchun; WO2015/108881; (2015); A1;,
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. 637348-81-3, name is 3-Bromo-5-iodopyridin-2-ol, the common compound, a new synthetic route is introduced below. COA of Formula: C5H3BrINO

To a stirring suspension of 18 (see Example 4 above) (0.906 g, 3.0 mmol), 2-(tert-butyl-dimethyl-silanyloxy)ethanol (0.554 g, 3.15 mmol) and PPh3 (0.944 g, 3.6 mmol) in 20 mL of THF at -10 0C was added dropwise of diisopropylazodicarboxylate (DIAD) (0.728 g, 3.6 mmol) in 10 mL of THF. The ice-salt bath was removed and the reaction was kept at r.t. 2 h. The reaction solution was concentrated and purified by FC (EtOAc/Hexanes, 5/95) to afford 2-(tert-butyl-dimethyl-siianyloxy)ethoxy-3-bromo-5-iodorhoyridine, a colorless viscous liquid (0.995 g, 72%). 1H NMR £8.23 (d, IH, J= 2.0 Hz), 8.05 (d, IH, J= 2.0 Hz), 4.42 (t, 2H, J= 4.9 Hz), 3.98 (t, 2H, J= 4.9 Hz), 0.90 (s, 9H), 0.10 (s, 6H). HRMS calcd for C12H18BrINO2Si (M-CH3+), 441.9335; found, 441.9312.

The synthetic route of 637348-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; WO2007/126733; (2007); A2;,
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Reference of 99368-68-0, 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 99368-68-0, name is 6-Chloro-5-(trifluoromethyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 120 6-chloro-5-(trifluoromethyl)pyridine-3-sulfonyl chloride; Under ice-cooling, thionyl chloride (4 mL) was added dropwise over 20 min to water (27 mL). The mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, 6-chloro-5-(trifluoromethyl)pyridine-3-amine (1.14 g) was added to concentrated hydrochloric acid (9 mL) with stirring under ice-cooling, and concentrated hydrochloric acid (9 mL) was further added. A solution of sodium nitrite (0.44 g) in water (6 mL) was added dropwise over 10 min. The reaction mixture was gradually added at 5 C. to the above-mentioned sulfur dioxide-containing solution added with cuprous chloride (15 mg). Under ice-cooling, the mixture was further stirred for 30 min, and the precipitate was collected by filtration and washed with water. The obtained precipitate was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1?9:1) to give the title compound as an orange solid (yield 437 mg, 27%). 1H-NMR (CDCl3) delta: 8.58 (1H, m), 9.18 (1H, m).

According to the analysis of related databases, 99368-68-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2007/60623; (2007); A1;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 16205-47-3, 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 16205-47-3, name is 7-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 10 Synthesis of (S)-(-)-N-(1-azabicyclo[2.2.2]oct-3-yl)-7-methylpyrazolo[1,5-a]pyridine-3-carboxamide A solution of 880 mg (5 mmol) of 7-methyl-3-pyrazolo[1,5-a]pyridinecarboxylic acid in 10 ml of thionyl chloride was heated under reflux for 30 minutes. Thionyl chloride was distilled off under reduced pressure and the residue was dissolved in 30 ml of methylene chloride. The resultant solution was added dropwise under ice cooling to a solution of 644 mg (5.1 mmol) of (S)-(-)-1-azabicyclo[2.2.2]octan-3-amine, which had been prepared in accordance with the procedure disclosed in Japanese Patent Application Laid-Open No. 196583/1988, in 30 ml of methylene chloride.

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 16205-47-3, 7-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid.

Reference:
Patent; Asahi Kasei Kogyo Kabushiki Kaisha; US5200415; (1993); A;,
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Pyridine | C5H5N – PubChem

Application of 76006-11-6, 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. 76006-11-6, name is 7-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, 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.

Amixture of 7-chloro-1H-pyrazolo[3,4-c]pyridine (200 mg, 1.30 mmol) and piperazine (1.12g, 13.02 mmol) was dissolved in EtOH (20 mL). The mixture was stirred at 80 C for 8 h under microwave radiation. The solution was purified by prep-HPLC (Boston C18 21*250mm 10.im, Mobile phase: A: 0.1 % trifluoroacetic acid; B: acetonitrile) to afford 7-(piperazin-1-yl)-1H-pyrazolo[3,4-c]pyridine (100 mg, 0.493 mmol) as a white solid. MS (EI, m/z): 204.2 [M+H]t ?HNMR (500 MFIz, DMSO-d6) 13.72 (s, 1H), 8.15 (s, 1H), 7.64 (d, J= 5.6 Hz, 1H), 7.04 (d, J = 5.4 Hz, 1H), 3.64 (s, 4H), 2.75 (d, J= 108.1 Hz, 4H).

According to the analysis of related databases, 76006-11-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; O’NEILL, David John; SAIAH, Eddine; KANG, Seong Woo Anthony; BREARLEY, Andrew; BENTLEY, Jonathan; (565 pag.)WO2018/89433; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63237-88-7 ,Some common heterocyclic compound, 63237-88-7, molecular formula is C8H6N2O2, 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.

Preparation 26PyrazoloH ,5-alpyridine-2-carbonyl chloride Pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (44.4mg, 0.274mmol) was suspended in dichloromethane (1 ml_) and treated with 1-Chloro-/V,/V,2-trimethyl-1 -propenylamine (109uL, 0.823mmol). The mixture was stirred at room temperature for 30 minutes during this time a solution was given. This solution was then used straight away.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63237-88-7, its application will become more common.

Reference:
Patent; PFIZER LIMITED; GLOSSOP, Paul Alan; PALMER, Michael John; ANDREWS, Mark David; WO2012/120398; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19346-43-1, 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 19346-43-1, name is 2-Fluoro-3-nitro-4-picoline. This compound has unique chemical properties. The synthetic route is as follows.

26. Preparation of 3-Amino-2-fluoro-4-methylpyridine To a solution of 10.1 g (65 mmol) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge) (2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was recovered, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid melting at 63-64 C. Nuclear Magnetic Resonance Spectrum (200 MHz (megaHertz), CDCl3): 1 H: 7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13 C: 152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5); 128.1 (d, J=27.1); 123.3, 16.4 (d, J=4.1).

According to the analysis of related databases, 19346-43-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DowElanco; US5494887; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1461602-59-4, 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. 1461602-59-4, name is 3-(Methylamino)isonicotinic Acid, molecular formula is C7H8N2O2, 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-(Methylamino)isonicotinic acid (4.00 g, 26.3 mmol), 1-hydroxybenzotriazole (10.7 g, 78.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (15.1 g, 78.9 mmol) and ammonium chloride (5.63 g, 105 mmol) were dissolved in N,N-dimethylformamide (5 mL). The reaction solution was stirred at 25C for 24 hours. The reaction was quenched by adding water (100 mL). The mixture was extracted with isopropanol / chloroform (1:3) (50 mL x 2). The organic phases were combined and concentrated under reduced pressure. The residue was added with dichloromethane / methanol (10:1, 30 mL), stirred for 10 minutes, filtered and the filter cake was dried to give 3-(methylamino)isonicotinamide (3.50 g, as a yellow solid) with a yield of 88%. 1H NMR: (400 MHz, DMSO-d6) delta 8.12-8.06(m, 2H), 7.80(d, J = 5.2 Hz, 1H), 7.62-7.61(br, 1H), 7.52-7.48(br, 1H), 7.43(d, J = 5.2 Hz, 1H), 2.84(d, J = 5.2 Hz, 3H).

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 1461602-59-4, 3-(Methylamino)isonicotinic Acid.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Lingyun; CHEN, Xiaoxin; ZHANG, Peng; LIU, Xing; ZHANG, Li; LIU, Zhuowei; CHEN, Shuhui; LONG, Chaofeng; (160 pag.)EP3299371; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3430-21-5 ,Some common heterocyclic compound, 3430-21-5, molecular formula is C6H7BrN2, 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 11A 5-bromo-2-hydroxy-3-methylpyridine 2-Amino-5-bromo-3-methylpyridine (5.0 g, 26.7 mmol) in 2.6M H2SO4 (70 mL) was treated with sodium nitrite (5.0 g, 72.5 mmol) in water (10 mL) dropwise at 0 C. The mixture was allowed to warm to ambient temperature and stir for 1.5 hours. The mixture was filtered and the filtercake washed with cold water. The filtercake was dissolved in dichloromethane (100 mL), dried (MgSO4), and concentrated to provide the title compound (4.2 g, 84% yield). MS (DCI/NH3) M/z 188/190 (M+H)+.

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. 3430-21-5, 5-Bromo-3-methylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Schrimpf, Michael R.; Tietje, Karin R.; Toupence, Richard B.; Ji, Jianguo; Basha, Anwer; Bunnelle, William H.; Daanen, Jerome F.; Pace, Jennifer M.; Sippy, Kevin B.; US2002/19388; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55052-27-2, 6-Chloro-1H-pyrrolo[2,3-b]pyridine, 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 C7H5ClN2, blongs to pyridine-derivatives compound. Computed Properties of C7H5ClN2

PREPARATION 58 6-Methyl-1 H-pyrrolo[2,3-b]pyridine The title compound of Preparation 57 (1 .00 g, 6.55 mmol), 2, 4, 6-trimethyl-1 ,3,5,2,4,6- trioxatriborinane (1 .0 ml, 7.2 mmol) and potassium carbonate (2.72 g, 19.7 mmol) were suspended in 13 ml dimethoxyethane in a microwave reactor and submitted to three vacuum-argon cycles. [1 , 1 ‘-Bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (0.29 g, 0.33 mmol) was added and the resulting mixture was submitted to three further vacuum-argon cycles. The mixture was stirred at 120C for 2h under microwave irradiation. The mixture was allowed to cool and was filtered through Celite, eluting with ethyl acetate. The filtrate was evaporated under reduced pressure and the residue was purified using the Isolera Purification System (ethyl acetate-hexane gradient, 0:100 rising to 50:50) to give 0.57 g (4.31 mmol, 65%) of the title compound as a beige solid. Purity 98%. 1 H N MR (300 MHz, CHLOROFORM-d) delta ppm 10.87 (br. s., 1 H), 7.86 (d, J=7.63 Hz, 1 H), 7.29 (dd, J=3.52, 2.35 Hz, 1 H), 6.97 (d, J=7.63 Hz, 1 H), 6.47 (dd, J=3.52, 1 .76 Hz, 1 H), 2.69 (s, 3 H). HPLC/MS (15 min) retention time 2.57 min. LRMS: m/z 133 (M+1 ).

The synthetic route of 55052-27-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; VIDAL JUAN, Bernat; ALONSO DIEZ, Juan Antonio; BUIL ALBERO, Maria Antonia; EASTWOOD, Paul Robert; ESTEVE TRIAS, Cristina; LOZOYA TORIBIO, Maria Estrella; ROBERTS, Richard Spurring; VIDAL GISPERT, Laura; GONZALEZ RODRIGUEZ, Jacob; MIR CEPEDA, Marta; WO2013/10880; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem