Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1314353-68-8, 5-Cyclopropylpyridin-3-amine, 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 5-Cyclopropylpyridin-3-amine, blongs to pyridine-derivatives compound. Quality Control of 5-Cyclopropylpyridin-3-amine

At 0 C, to a solution of 5-cyclopropylpyridin-3-amine (2.08 g, 15.49 minol) in tetrahydrofuran (30 mL) was added a solution of NaHMDS (6.84 g, 37.30 minol) in tetrahydrofuran (20 mL) dropwise over 10 min period. The resulting solution was stirred for 1 h at 0 C, and then was added by a solution of di-tert-butyl dicarbonate (4.85 g, 22.20 minol) in tetrahydrofuran (25 mL) dropwise. The resultingminxture was stirred for additional 2 h at room temperature. When the reaction was done, it was quenched by the addition of sat. NH4C1 solution (100 mL). The resultingminxture was extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with MeOH in EtOAc (0% to 80% gradient) to yield tert-butyl N-(5- cyclopropylpyridin-3-yl)carbamate as white solid (2.52 g, 69%). MS: m/z = 235.0 [M+Hj.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1314353-68-8, 5-Cyclopropylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; SHERER, Brian A.; BRUGGER, Nadia; (546 pag.)WO2017/106607; (2017); 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. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline, the common compound, a new synthetic route is introduced below. SDS of cas: 185017-72-5

a) 1-(2-Chloro-6-methylpyridin-3-yl)cyclobutanol A suspension of molecular sieves (4 A) and 3-bromo-2-chloro-6-methylpyridine (CAN 185017-72-5, 5 g, 24.2 mmol) in THF (50 mL) was cooled to -15 C. 1.3 M isopropyl magnesium chloride lithium chloride complex solution in THF (19.6 mL, 25.4 mmol) was added within 30 mm. Stuffing was continued for 1 h at -15 C. Cyclobutanone (1.87 g, 2.00 mL, 26.6 mmol) was slowly added. Stirring was continued for 2 h at -15 C and for further 2 h at 0 C. Water (2.5 mL) was added, the mixture was concentrated in vacuo, and poured onto sat. aqueous NH4C1 solution. The mixture was extracted with EtOAc (2 x 100 mL).The combined extracts were washed with ice water (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 140 g, heptane / EtOAc 0-40% in 120 mm.) to give the title compound (3.33 g, 70%) as white solid, MS (ESI): mle = 198.1 [MHi.

The synthetic route of 185017-72-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FREI, Beat; GOBBI, Luca; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; WO2014/86705; (2014); A1;,
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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H5BrClN

[0415] To a stirred solution of sodium metal (4.46 g, 194 mmol) in MeOH (200 mL) under an argon atmosphere was added 3-bromo-2-chloro-6-methylpyridine (20 g, 97 mmol) at 0 C. The reaction mixture was stirred at 100 C for 4 h in a sealed tube. After consumption of starting material (by TLC), volatiles were evaporated in vacuo. The residue was quenched with water (200 mL) and extracted with EtOAc (2 x 250 mL). The combined organic extract was dried over sodium sulfate, filtered and concentrated in vacuo to obtain 3-bromo-2- methoxy-6-methylpyridine (18 g, 92%) as colorless liquid.?H-NMR (CDC13, 400 MHz): 7.61 (d, 1H), 6.60 (d, 1H), 3.99 (s, 3H), 2.39 (s, 3H); LCMS:99.6%; 201.8 (M+1); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 jtm); RT 2.67 mm; mobile phase: 0.025% Aq TFA+5% ACN: ACN+5% 0.025% Aq TFA; T/B%: 0.01/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: 10% EtOAc/ Hexane (R1 0.7). Synthesis of 5-bromo-6-methoxypicolinic acid:

With the rapid development of chemical substances, we look forward to future research findings about 185017-72-5.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 933721-91-6, Imidazo[1,2-a]pyridin-8-ylmethanamine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A solution of compound 5e (60 mg, 0.15 mmol) and compound 19c (26 mg, 0.18 mmol) in ethanol (0.5 mL) was irradiated at 180 C. in a microwave instrument for two 30 min intervals, then concentrated. The residue was dissolved in methyl sulfoxide and purified by reversed-phase chromatography to furnish the title compound 188 as its trifluoroacetate salt. 1H NMR (methanol-d4): delta 8.66 (d, 1H, J=6.8 Hz), 8.20 (d, 1H, J=2.2 Hz), 8.01 (d, 1H, J=2.2 Hz), 7.46 (d, 1H, J=7.4 Hz), 7.33 (d, 2H, J=8.6 Hz), 7.28 (t, 1H, J=7.0 Hz), 7.15 (d, 2H, J=8.6 Hz), 6.88 (d, 2H, J=8.8 Hz), 6.83 (d, 2H, J=8.8 Hz), 5.15 (s, 2H), 4.96 (s, 2H), 4.88 (s, 2H), 3.78 (s, 3H), 3.75 (s, 3H); HRMS m/z (M+H)+ calcd for C27H27N6O4 499.2094, found 499.2052.

The synthetic route of 933721-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Flores, Christopher M.; Wade, Paul R.; US2011/319400; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1220910-89-3 , The common heterocyclic compound, 1220910-89-3, name is Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate, molecular formula is C21H17FN6O2, 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.

To the kettle was added tetrahydrofuran (20 L)And benzyl N- [3-fluoro-4- [6- (2-methyl- 2H- tetrazolium- 5 -yl) -3-pyridyl] phenyl] carbamateCompound (II) (1 Kg, 2.47 mol),0 ~ 30 C After mixing,1,3-Dimethyl-3,4,5,6-tetrahydro-2-pyrimidone was added sequentially (DMPU, 0.63 Kg, 4.94 mol, 2 equivalents),Lithium tert-butoxide (0.396 Kg, 4.94 mol, 2 equivalents)Add R-glycidyl butyrate(0.39 Kg, 2.72 mol, 1.1 equivalents)0 ~ 30 C for 15 hours.After the reaction,The reaction was quenched by adding a mass-volume ammonium chloride solution (1 Kg / 10 L)Concentrated under reduced pressure,The residue was added to methanol (10 L)Stirred for 0.5 hours to give suction filtration,The filter cake was washed with methanol,45 ~ 50 C under vacuum to give a white solid(5R) -3- (4- (6- (2-methyl- 2H- tetrazolium- 5-yl) -3-pyridyl) -3- fluorophenyl) -5-hydroxymethyl oxazoline -2-one Compound (III) (0.87 Kg, yield: 95%).

The synthetic route of 1220910-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing You Ke Pharmaceutical Co., Ltd.; Nanjing You Ke Bio-pharmaceutical Co., Ltd.; Nanjing You Ke Bio-pharmaceutical Group Co., Ltd.; Li Shang; Che Xiaoming; Zhao Zanzan; Zhu Suhua; Xue Yuquan; Zhang Feng; (7 pag.)CN106317114; (2017); 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 89978-52-9, name is Ethyl 2-bromoisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 89978-52-9

In a 100 mL two-necked flask, 2.10 g of 2-bromo-4-carboxylatepyridine, 2.01 g of 3,5-dimethoxyphenylboronic acid, 4.86 g of potassium carbonate, and 0.66 g of tetrakis(triphenylphosphine)palladium, toluene were added. 60 mL, heated at 110 C for 20 hours. After cooling to room temperature, the solution was washed with water (3×60 mL). The organic layer was dried with anhydrous MgSO4, filtered and evaporated. Purification by column chromatography (eluent:Petroleum ether / ethyl acetate = 80:1) gave 1.47 g of a white product.The yield was 56%.

With the rapid development of chemical substances, we look forward to future research findings about 89978-52-9.

Reference:
Patent; Nanjing Tech University; Liu Rui; Li Yang; Shi Hong; Zhu Hongjun; Zhu Senqiang; Tang Meng; Lu Jiapeng; (21 pag.)CN109053815; (2018); A;,
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. 100202-78-6, name is 2-(Bromomethyl)-6-fluoropyridine. A new synthetic method of this compound is introduced below., SDS of cas: 100202-78-6

Mix (+/-)-N-(7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-isobutyramide (6.28 g, 18.8 mmol), 6-fluoro-2-bromomethylpyridine (3.93 g, 20.7 mmol), and Cs2CO3 (12.25 g, 37.6 mmol) in DMF (25 mL). Heat the reaction at 50 C. for 18 h. Cool, dilute with EtOAc, and wash with water (3×200 mL). Dry the organic layer (MgSO4) and concentrate to give 7.1 g crude material. Purify by silica gel chromatography (5-20% EtOAc/CH2Cl2). Obtain 4.0 g (56%) yellow-tan solid. MS (m/z): 377 (M+1), 375 (M-1).

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, 100202-78-6, 2-(Bromomethyl)-6-fluoropyridine.

Reference:
Patent; Gavardinas, Konstantinos; Green, Jonathan Edward; Jadhav, Prabhakar Kondaji; Matthews, Donald Paul; US2010/69404; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 98027-36-2, 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. 98027-36-2, name is 3-Amino-5-chloro-2-hydroxypyridine, molecular formula is C5H5ClN2O, 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.

b) tert-butyl 5-chloro-2-hydroxypyridin-3-ylcarbamate A mixture of 3-amino-5-chloropyridin-2-ol (20.0 g), di-tert-butyl dicarbonate (33.4 g), DMAP (848 mg), triethylamine (14.0 g) and DCM (200 mL) was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (9.50 g). MS: [M+Na]+267.1.

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 98027-36-2, 3-Amino-5-chloro-2-hydroxypyridine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); 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. 1190320-33-2, name is 6-Fluoro-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H5FN2

To a solution of 6-Fluoro-lH-pyrrolo[3,2-b]pyridine (CAS: 1190320-33-2 , 6.5 g, 47.74 mmol) in dry DMF (65 mL), was added NaH(3.82 g, 95.49 mmol) at 0C in portions, then the reaction mixture was stirred at room temperature for lh. Methyl iodide (5.30 mL, 95.49 mmol) was added at 0C, then stirred at room temperature for 2h. After the consumption of starting material, reaction mixture was cooled to 0C, added water and extracted with ethyl acetate (2X 100 mL)). The combined organic layers were washed with brine, dried over sodium sulphate and evaporated under reduced pressure to get crude. Crude was purified by column chromatography (230/400 mesh, 30% ethyl acetate in pet-ether) to get desire compound Xllla as white solid (6 g, 85%). LC_MS Calc. for C8H7FN2 150.16; obtained: 151.11H NMR (400 MHz, DMSO-D6): delta 8.33 (s, 1H), 7.89-7.86 (m, 1H), 7.64 (d, 1H, J=2.8 Hz), 6.58 (s, 1H), 3.80 (s, 3H).

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, 1190320-33-2, 6-Fluoro-1H-pyrrolo[3,2-b]pyridine.

Reference:
Patent; BUGWORKS RESEARCH INDIA PVT LTD; PEER MOHAMED, Shahul Hameed; BHARATHAM, Nagakumar; KATAGIHALLIMATH, Nainesh; SHARMA, Sreevalli; NANDISHAIAH, Radha; (113 pag.)WO2017/199265; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1228880-68-9, Adding some certain compound to certain chemical reactions, such as: 1228880-68-9, name is Methyl 3-bromo-5-methylpicolinate,molecular formula is C8H8BrNO2, 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 1228880-68-9.

Step A: Methyl 3-fluoro-5′-methyl-[2,3′-bipyridine]-2′-carboxylate. In a sealed tube 3-fluoro-2-(tributylstannyl)pyridine (2.87 g, 6.9 mmol) was added to a stirred solution of methyl 3-bromo-5-methylpicolinate (1.46 g, 6.3 mmol), Pd(PPh3)4 (367 mg, 0.3 mmol), copper(I) iodide (60 mg, 0.3 mmol) and lithium chloride (267 mg, 6.3 mmol) in toluene (19 mL) while the solution was bubbled with nitrogen. The reaction mixture was stirred at 120 C. overnight and then diluted with water and extracted with ethyl acetate. The organic layers were dried over MgSO4, filtered and concentrated. The crude was purified via silica gel chromatography (0-4% MeOH in DCM) to afford the title compound (1.24 g, 79%). MS (ESI) mass calcd. for C13H11FN2O2, 246.1. m/z found 247.0 [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. 1228880-68-9, Methyl 3-bromo-5-methylpicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Shireman, Brock T.; Lebold, Terry P.; Dvorak, Curt A.; Coate, Heather R.; Ziff, Jeannie M.; Preville, Cathy; Gelin, Christine; Chen, Gang; (123 pag.)US2016/75696; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem