Pyridine-derivatives

Reference of 167837-43-6, 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 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows.

EDC (231 mg, 1.2 mmol) was added to a solution of (4-3-(6-AMINO-PYRIDIN-3- yl) acrylic acid (164 mg, 1.0 mmol), (2-isopropoxy-3-methoxy-benzyl) methylamine (230 mg, 1.1 mmol), HOBT’H20 (149 mg, 1.1 mmol) and DIPEA (525 UL, 3.0 mmol) in dry DMF (10 mL). After 18 hr of stirring, the mixture was diluted with water (60 mL) and extracted with EtOAc (2X20 mL). The organic layer was washed with brine (2×30 mL), dried and evaporated. Flash chromatography (silica 1-3% MEOH in CH2CL2) of the residue furnished pure free base which was dissolved in CHUCK (10 mL). After addition OF HCL (1.5 mL, 1M in ether) the solvents were evaporated; the residue was washed with ether and dried to afford the title compound (180 mg, 46%). 1H NMR (300 MHz, DMSO-D6) 8 8.31 (m, 3H), 7.46 and 7.45 (rotamers, 2d, J= 15.4 Hz, 1H), 7.23 and 7.17 (rotamers, 2d, J= 15.4 Hz, 1H), 6.99 (m, 3H), 6.62 (m, 1H), 4.76 and 4.63 (rotamers, 2s, 2H), 4. 51 (M, 1H), 3.79 (s, 3H), 3.06 and 2.85 (rotamers, 2s, 3H), 1.22 (d, J= 6. 1Hz, 3H) 1.21 (d, J= 6. 1Hz, 3H). MS (ESI) INLE 356 (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 167837-43-6, (E)-3-(6-Aminopyridin-3-yl)acrylic acid.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 204378-41-6, 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 204378-41-6, name is Methyl 6-chloro-4-methoxypicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 6-chloro-4-methoxypicolinate 25 (500 mg, 2.48 mmol) and pentan-3-ylzinc(II) bromide (10 mL of a 0.5 M solution in THF) in dioxane (10 mL) Pd(dppf)Cl2 (21 mg, 25 mol) was added under argon. The mixture was stirred at 75°C for 18 h. The mixture was cooled the rt and the reaction was quenched by carefully adding water (10 mL). The mixture was filtered and the filtrate was extracted twice with EA (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. During the reaction the methyl picolinate was transformed to the pent-3-yl picolinate, and formation of the 6-(pent-2-yl)picolinate isomer complicated the purification and compromised the yield. Hence, the crude product was purified by CC on silica gel eluting with heptane:EA 9:1 to give pentan-3-yl 4-methoxy-6-(pentan-3-yl)picolinate 26 (145 mg, 20percent) as a pale yellow oil

According to the analysis of related databases, 204378-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bolli, Martin H.; Lescop, Cyrille; Birker, Magdalena; De Kanter, Ruben; Hess, Patrick; Kohl, Christopher; Nayler, Oliver; Rey, Markus; Sieber, Patrick; Velker, Joerg; Weller, Thomas; Steiner, Beat; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 326 – 341;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 947179-03-5, 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. 947179-03-5, name is Ethyl 4-bromo-6-methylpicolinate, molecular formula is C9H10BrNO2, 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.

d) A solution of 4-bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester (2.42 g, 9.91 mmol) in 6 N aq. HCl (100 mL) is stirred at 65 C. for 18 h. The solvent is evaporated and the residue is dried under HV, suspended in DCM, filtered and dried again under HV to give 4-bromo-6-methyl-pyridine-2-carboxylic acid (2.50 g) as a hydrochloride salt in form of a white powder; LC-MS: tR=0.46 min, [M+1]+=215.93.

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 947179-03-5, Ethyl 4-bromo-6-methylpicolinate.

Reference:
Patent; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Mueller, Claus; Nayler, Oliver; Steiner, Beat; Velker, Jorg; US2011/212998; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid. A new synthetic method of this compound is introduced below.

[0553] To a cooled solution of /V,/V-dicyclohexylcarbodiimide (7.36 g, 35.69 mmol,) in dichloromethane (120 mL) was added DMAP (3.17 g, 25.96 mmol) at 0 C, followed by 2-(2- chloropyridin-3-yl)acetic acid (5.57 g, 32.45 mmol), and the resulting mixture was stirred at 0 C for 5 min. te t-Butanol (9.3 mL, 97.337 mmol) was then added to the reaction, and the resulting mixture was allowed to warm to room temperature with stirring for 12 h. The reaction was then evaporated to dryness to give a residue, which was dissolved in diethyl ether (400 mL). The ether solution was then filtered through a pad of celite, which was washed with diethyl ether (2 c 200 mL). The combined filtrates were washed sequentially with 1 M aqueous NaOH (300 mL), 2 N aqueous HC1 (300 mL), water (300 mL) and brine (200 mL). The organic layer was then dried over Na2S04, filtered and evaporated to dryness to give the crude product as a residue. Purification by flash column chromatography eluting with a gradient of ethyl acetate (5-20%) in hexane to afford the desired product as beige solid (5.25 g, 71.0%). UPLC-MS (Acidic Method, 2 min): rt = 1.08 min, m/z 228.1 [M+H]+. NMR (400 MHz, CDCb) d ppm 8.31 (dd, J=4.77Hz, 2.01Hz, 1H), 7.63 (dd, J=7.53Hz, 2.01Hz, 1H), 7.22 (dd, =7.53Hz, 4.77Hz, 1H), 3.68 (s, 2H), 1.46 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; TSAI, Kenneth, Y.; KINCAID, John; SARIN, Kavita, Yang; (319 pag.)WO2020/106303; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 443956-08-9, 6-Bromo-2-nitropyridin-3-ol, 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, SDS of cas: 443956-08-9, blongs to pyridine-derivatives compound. SDS of cas: 443956-08-9

Compound I-2 (1 g, 4.6 mmol) was added to a three-necked flask,Dissolved with 20 mL of ethanol,After replacing the nitrogen three times,To this was added zinc dust (1.5 g, 22.9 mmol) andAmmonium chloride (2.46 g, 46 mmol),Replace nitrogen again;50 under the conditions of reaction 16h,(CH2Cl2: CH3OH = 25: 1). The reaction solution was filtered and the filtrate was collected. After concentration under reduced pressure, the residue was purified by petroleum ether / ethyl acetate (5: 1)The grayishl solid was the target product I-3 (524 mg, 60%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,443956-08-9, 6-Bromo-2-nitropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Normal University; Zhang Huabei; Wang Huan; Fang Yu; Liu Jianping; Wang Shuxia; (32 pag.)CN107188900; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 669066-89-1, 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. 669066-89-1, name is 3-Amino-5-bromopicolinamide, molecular formula is C6H6BrN3O, 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) 3-Amino-5-bromopicolinic acid. A mixture of 3-amino-5- bromopicolinamide (28.2 g, 0.13 mol) and concentrated HCl (361 mL) was heated at reflux for 12 hours. The reaction mixture was left to reach room temperature, and the solid which precipitated was filtered. The filter cake was dissolved in water, and the pH of the aqueous solution was adjusted to pH = 4 with saturated NaOAc, and extracted with EtOAc (3 x). The combined organic layers were dried over anhydrous MgSO4, and filtered. The filtrate was evaporated under reduced pressure, and the residue was dried in vacuo to afford the title compound as a solid.

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 669066-89-1, 3-Amino-5-bromopicolinamide.

Reference:
Patent; AMGEN INC.; WO2008/130600; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1221171-96-5, 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 1221171-96-5, name is 2-Chloro-4-iodo-6-(trifluoromethoxy)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-Chloro-6-trifluoromethoxy isonicotinic acid (43); At 0 0C, butyllithium (1.56 M in hexane, 4.0 mL, 6.2 mmol, 0.67 eq) was added dropwise to a solution of butylmagnesium chloride (2M in THF, 1.5 mL, 3.0 mmol, 0.33 eq) in THF (8 mL), followed after 10 min by a solution of 2-chloro-4-iodo-6- trifluoro?iepsilonthoxypyridinepsilon (42, 3.0 g, 9.3 mmol, 1 eq) in THF (5 mL). After 10 min the reaction mixture was poured onto an excess of freshly crushed dry ice before being treated with an aqueous solution of sodium hydroxide (5%, 15 mL). The resulting aqueous layer was collected, washed with diethylether (10 mL) and acidified to pH 4 by dropwise addition of hydrochloric acid (6 N, 5 mL). After extraction with ethyl acetate (3 x 10 mL), the combined organic layers were dried over sodium sulfate before being evaporated to afford pure 2-chloro-6-trifluoromethoxy isonicotinic acid (43, 1.6 g, 6.6 mmol, 71%) as a white powder; m.p. 65-68 0C.1H NMR (CDCl3, 300 MHz): delta = 10.12 (br s, 1 H), 7.88 (d, J = 0.9 Hz, 1 H), 7.56 (d, J = 0.9 Hz, 1 H). – 19F NMR (CDCl3, 282 MHz): delta = -57.3 – 13C NMR (CDCl3, 75 MHz): delta = 167.6, 156.3, 150.4, 143.0, 122.5, 120.2 (q, J = 260 Hz), 113.5. – C7H3ClF3NO3 (241): calcd. (%) C 34.81, H 1.25, N 5.80; found C 34.64, H 1.55, N 5.76.

According to the analysis of related databases, 1221171-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63237-88-7, 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 63237-88-7 as follows.

General procedure: A solution of P(OMe)3 (1.5mmol) in DCM (10mL) was cooled with an ice bath, then I2 (1.5mmol) was added. After the solid iodine was completely dissolved, corresponding acid (1.2mmol) and Et3N (3.0mmol) were added in sequential order, and the solution was stirred for 15min in a cooling bath. Intermediate 5 (1.0mmol) was added and the mixture was stirred for 15min. After removing the cooling bath, the reaction mixture was stirred for 3.5hat room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10mL) three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (100:1 to 50:1, v/v) to give the product as a white solid.

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:
Article; Bai, Renren; Shi, Qi; Liang, Zhongxing; Yoon, Younghyoun; Han, Yiran; Feng, Amber; Liu, Shuangping; Oum, Yoonhyeun; Yun, C. Chris; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 464 – 475;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 112110-07-3, 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 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

REFERENCE EXAMPLE 1 Preparation of N-(2,6-difluorobenzoyl)-N’-(5-trifluoromethyl-3-pyridyl)urea (compound No. 1) 1.0 g of 3-amino-5-trifluoromethylpyridine was dissolved in 5 ml of dioxane, and a solution of 1.35 g of 2,6-difluorobenzoylisocyanate in 2 ml of dioxane was dropwise added to the former solution. The reaction was carried out at room temperature for 1 hour, while stirring. After the completion of the reaction, the reaction product was pourred into about 100 ml of water to precipitate crystals. The precipitate was filtered and washed with methanol, followed by drying, thus obtaining 1.73 g of N-(2,6-difluorobenzoyl)-N’-(5-trifluoromethyl-3-pyridyl)urea (melting point: 233 to 235 C.).

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 112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US4762928; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8 , The common heterocyclic compound, 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, 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.

A mixture of 1-11 (4.30 g, 12.57 mmol) , bis (pinacolato) diboron (3.82 g 15.07 mmol) and KOAc (2.94 g, 37.69 mmol) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1- bis (diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (0.307 g, 0.376 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100C for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL) , followed by extraction with ethyl acetate (50 mL x 3) . The combined organic layers were washed with brine (50 mL) , dried over anhydrous Na2SC> and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50% EtOAc in hexanes to give the desired product Intermediate 1- XIII as a mixture of minor boronate ester together with major boronic acid . (4.8 g, crude yield 98%) as a yellow solid; LCMS (for boronate ester) : m/z 390.2 [M+l]; LCMS (for boronic acid) : m/z 308.1 [M+l] .

The synthetic route of 153747-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; BHOSALE, Sandeep; NAIK, Keshav; SALUNKHE, Videsh; MUNOT, Yogesh; BHUNIYA, Debnath; (284 pag.)WO2015/88045; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem