Category: pyridine-derivatives

Application of 88912-21-4, 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. 88912-21-4, name is 6-Chloro-4-methoxypicolinic acid. A new synthetic method of this compound is introduced below.

Synthesis Example 16 Synthesis of N-[(2-Trifluoromethoxyphenyl)sulfonyl]-6-chloro-4-methoxy-2-pyridinecarboxamide [Compound (I-795)] Using 2-trifluoromethoxybenzenesulfonamide [Compound (III-12)] (0.23 g, 0.96 mmol) and 6-chloro-4-methoxypicolinic acid [Compound (II-75)] (0.18 g, 0.96 mmol), the Compound (I-795) was synthesised according to the process of Synthesis Example 3. White solid, yield: 0.20 g, percent yield: 52%, m.p.: 135-138 C. IR KBr cm-1: 3372, 1728, 1598, 1440, 1356, 1262, 1192. 1H-NMR (60 MHz, CDCl3, delta): 3.80 (3H, s, OCH3), 6.9 (1H, d, J=2 Hz, pyridine ring H), 7.28-7.65 (3H, m, aromatic ring H), 7.46 (1H, d, J=2 Hz, pyridine ring H), 8.2 (1H, dd, J=2 Hz, 8 Hz, aromatic ring H), NH indistinctness.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88912-21-4, 6-Chloro-4-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Kureha Kagaku Kogyo K.K.; US6610853; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1137-68-4, 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. 1137-68-4, name is 2-(2-Pyridyl)benzimidazole. A new synthetic method of this compound is introduced below.

Under N2, solid NaH (60% dispersed in mineral oil, 0.120 g) and 2-(2-pyridyl)benzimidazole (0.680 g, 0.0035 mol) in 20 mL of anhydrous DMF was stirred at 80 C for 2 h. The resulting solution was cooled to room temperature and 9-(4-(bromomethyl)penyl)-9H-carbazole (1.400 g, 0.0042 mol) was added. The mixed solution was stirred at 80 C for 36 h. After completing, the reaction mixture was poured into 100 mL of cool water, and was extracted with dichloromethane (3 × 50 mL). The organic phase was washed with water and dried over anhydrous MgSO4. After removal of solvent, the residue was purified by column chromatography using ethyl acetate/petroleum ether (1: 4, v/v) as the eluent to give a white powder. Yield: 81%. m.p.:186-188 C. IR (KBr pellet cm-1): 3041 (Aryl-CH), 2931 (-CH2-), 1614, 1456, 1328, 1150, 750. 1H NMR(CDCl3, delta, ppm): 8.70 (d, 1H, J = 7.4 Hz, Aryl-H), 8.50 (d, 1H, J = 8.0 Hz, Aryl-H), 8.11 (d, 2H, J = 7.6 Hz, Aryl-H), 7.92-7.86 (m, 2H, Aryl-H), 7.48-7.41 (m, 5H, Aryl-H), 7.38-7.33 (m, 7H, Aryl-H), 7.25 (t, 2H, J = 8.8 Hz, Aryl-H), 6.32 (s, 2H, N-CH2-Ar). Anal. Calc. for C31H22N4 (%): C, 82.64; H, 4.92; N, 12.44. Found: C, 82.38; H, 5.01; N, 12.52.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1137-68-4, 2-(2-Pyridyl)benzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yu, Tianzhi; Chai, Haifang; Zhao, Yuling; Zhang, Chengcheng; Liu, Peng; Fan, Duowang; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 109; (2013); p. 179 – 185;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 24100-18-3, 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. 24100-18-3, name is 2-Bromo-3-methoxypyridine. A new synthetic method of this compound is introduced below.

Step A 2-Bromo-3-methoxy-6-nitropyridine To a 500 mL round bottomed flask fitted with a Teflon stir bar and a thermometer was added 90 mL of concentrated sulphuric acid and 37.6 g of 2-bromo-3-methoxypyridine (200 mmol). The flask was warmed in an oil bath to 60 C. Added slowly over 1h 16.5 mL (350 mmol) of fuming nitric acid (90%, d=1.50). Maintain the temperature between 60 and 70 during the addition. Stir at 60 for 3h after the addition was complete, then at room temperature overnight. By TLC (70/30 hex/EtOAc) is consumed. The product mixture was poured into 600 mL of ice/water, from which the product precipitated. This material was filtered, washed with 3*200 mL of cold water and then 100 mL of saturated sodium bicarbonate. After drying in the filter funnel in a stream of air, the remaining water was removed under reduced pressure, to give 16.5 g of a solid. H NMR (400 MHz, CDCl3): delta 8.27(d, J=8 Hz,1H); 6.32(d, J=8 Hz,1H); 4.06(s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24100-18-3, 2-Bromo-3-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US5929094; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6937-03-7, 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. 6937-03-7, name is Methyl 2-aminoisonicotinate. A new synthetic method of this compound is introduced below.

(2-Amino-pyridin-4-yl)-methanol (2-4) 2-Amino-isonicotinic acid methyl ester (6.0 g, 39.4 mmol) was dissolved in 80 mL anhydrous THF in a flame dried round bottom flask under nitrogen gas. The solution was cooled to -45° C. and LAH (39.4 mL, 1M in THF) was added slowly. The reaction was allowed to warm to 0° C. and was quenched by the addition of 15 mL of 1M NaOH (aq). The solution was filtered and the solid was washed with THF. The filtrate was concentrated to afford the pure product. 1H NMR (DMSO-d6) delta7.79 (d, 1H, J=5.2 Hz), 6.41 (s, 1H), 6.38 (d, 1H, J=5.9 Hz), 5.79 (bs, 2H), 5.19 (t, 2H, J=5.7), 4.35 (d, 2H, J=5.6 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6937-03-7, Methyl 2-aminoisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Ren, Yu; Karki, Shyam B.; Zhao, Matthew M.; Bidodeau, Mark T.; US2004/23981; (2004); 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. 1052714-46-1, name is 6-Bromo-5-fluoropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 6-Bromo-5-fluoropicolinic acid

Synthesis of methyl 6-bromo-5-fluoropicolinate To a solution of 6-bromo-5-fluoropicolinic acid (1.0 equiv.) in methanol (0.2 M) was added H2SO4 (4.2 equiv.) and the reaction was stirred at room temperature for two hours. Upon completion of the reaction as monitored by LC/MS, the reaction was diluted with ethyl acetate and quenched slowly with saturated aqueous NaHCO3. The reaction was poured into a separatory funnel and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate, filtered, and concentrated in vacuo to provide methyl 6-bromo-5-fluoropicolinate as a white solid (>99%). LC/MS=233.9/235.9 (M+H), Rt=0.69 min.

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, 1052714-46-1, 6-Bromo-5-fluoropicolinic acid.

Reference:
Patent; BURGER, Matthew T.; HAN, Wooseok; LAN, Jiong; NISHIGUCHI, Gisele; US2010/56576; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 588729-99-1, 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. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, molecular formula is C5H4BrClN2, 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.

c) N-(5 -bromo-2-chloro-3 -pyridinyl)benzenesulfonamide. To a stirred solution of 3-amino-5-bromo-2-chloropyridine (24 mmol) in dichloromethane (50 mL) was added pyridine (37 mmol) followed by benzenesulfonyl chloride (35 mmol) drop wise over 5 min. The reaction mixture was stirred at room temperature for 18 h and evaporated to dryness in vacuo. The residue was purified by flash chromatography on silica gel (15% hexanes/dichloromethane then 0-5% ethyl acetate in 15% hexanes/dichloromethane). During evaporation of the solvents the product precipitated. The resultant slurry was diluted with hexanes, filtered, and dried under vacuum to give the title compound (2.89 g, 34%) as a white solid. MS (ES) m/e 346.7 (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 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/39140; (2009); 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. 52833-94-0, name is 2-Amino-5-bromonicotinic acid. A new synthetic method of this compound is introduced below., Recommanded Product: 2-Amino-5-bromonicotinic acid

To a mixture of 2-amino-5-bromonicotinic acid (1 g, 4.61 mmol) and (1-(1-(tert- butoxycarbonyl)piperidin-4-yl)-1H-pyrazol-4-yl)boronic acid pinacol ester (2.6 g, 6.91 mmol) in 25 mL of 1,4-dioxane/ water (3/1) was added K2CO3 (1.9 g, 13.8 mmol) followed by Pd(PPh3)4 (0.26 g, 0.23 mmol). The reaction mixture was heated at 100 C for 3 h, cooled to room temperature, and partitioned between water and ethyl acetate. Water layer was separated and adjusted to pH value around 5. The precipitate was collected by filtration and triturated in mixture of methanol and water. The precipitate was filtered. The wet cake was dried to afford 1.5 g of the title compound. The crude product was used for the next step without further purification. MS (ESI, m/z): 388.1 [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, 52833-94-0, 2-Amino-5-bromonicotinic acid.

Reference:
Patent; DONG-A SOCIO HOLDINGS CO., LTD.; KIM, Hadong; RYU, Ki Moon; PARK, Seong Jin; YOON, Taeyoung; JANG, Mi Yeon; KIM, Jin Kwan; (419 pag.)WO2018/71343; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 871836-51-0, 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.871836-51-0, name is 4-Chloro-1H-pyrazolo[4,3-c]pyridine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

To a solution of 4-chloro-IH-pyrazolo[4,3-clpyridine (100 mg, 0.6Smmoi) (3 mL) was added NaI-l (78 mg, 1.95 mmol, 60 wt% in oil) at 0C under N2. The mixture was stirred at 0C for 40 minutes. Mel (277 mg, 1,95 mmol) was added at 25C. The mixture wasstirred for another 2 hours. The mixture was quenched with saturated Ni-14C1 aqueous solution and extracted with ELOAc (20 mL x 3). The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by Prep-HPLC to give the title compound 56 (50.2 mg) as yellow oil, 57 (30 mg) as yellow oil. LRMS miz (M+H) 168.1, 170.1 found, 168.0, 170.1 required.

The chemical industry reduces the impact on the environment during synthesis 871836-51-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 769-28-8, Adding some certain compound to certain chemical reactions, such as: 769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile,molecular formula is C8H8N2O, 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 769-28-8.

A 100 mL Teflon-sealed flask was charged with the 2-pyridone 1m(296 mg, 2.0 mmol), diaryliodonium salts 2r (1.695 g, 3.0 mmol, 1.5equiv), and Cs2CO3 (975 mg, 3.0 mmol, 1.5 equiv) under air atmosphere.DCE (20 mL) was then added to the flask. The reaction mixturewas stirred at 120 C until the 2-pyridone 1m was consumedcompletely (monitored by TLC). At this time, the solvent was removedin vacuo and the residue was purified by flash column chromatography(the crude residue was dry loaded on silica gel, 1:10 EtOAc/PE) toprovide the desired product 5; yield: 485 mg (83%); white solid; mp102-103 C.IR (film): 3073, 2922, 2229, 1600, 1449, 1327, 1179, 799 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.54-7.48 (m, 3 H), 7.39 (d, J = 7.2 Hz,1 H), 6.86 (s, 1 H), 2.54 (s, 3 H), 2.37 (s, 3 H). 13C NMR (100 MHz, CDCl3): delta = 126.8, 161.1, 155.1, 152.9, 132.3 (q, J =32.1 Hz), 129.9, 124.9, 122.2 (q, J = 269.1 Hz), 121.9 (q, J = 3.6 Hz),119.7, 118.8 (q, J = 3.6 Hz), 114.3, 95.3, 24.4, 20.2.HRMS (ESI): m/z (M + H)+ calcd for C15H12F3N2O: 293.0902; found:293.0891.

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. 769-28-8, 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Xiao-Hua; Ye, Ai-Hui; Liang, Cui; Mo, Dong-Liang; Synthesis; vol. 50; 8; (2018); p. 1699 – 1710;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17228-69-2 ,Some common heterocyclic compound, 17228-69-2, molecular formula is C6H6ClNO, 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 suspension of 2-chloro-4-methoxypyridine (250 mg; commercial), 2-benzyloxy- 5-formylphenylboronic acid (455 mg; commercial), K2C03 (1.65 g) in water (3 mL) and DMF (12 mL) was degassed with nitrogen, treated with bis(triphenylphosphine)palladium(II) di chloride (48 mg) and heated for 3 h at 100C. The reaction mixture was evaporated under reduced pressure and the residue was partitioned between water and EA. The aq. layer was extracted with EA. The combined org. layers were washed with water and brine, dried over MgS04; evaporated under reduced pressure and purified by CC (Hept to Hept/EA 2:3) to yield a light yellow solid (309 mg; 60% yield). MSI (ESI, m/z): 320.1 [M+H+]; tR = 0.66 min.

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. 17228-69-2, 2-Chloro-4-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CREN, Sylvaine; FRIEDLI, Astrid; HUBSCHWERLEN, Christian; RUEEDI, Georg; ZUMBRUNN, Cornelia; WO2014/170821; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem