Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 86847-84-9, N-(6-Chloropyridin-2-yl)pivalamide, 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: 86847-84-9, blongs to pyridine-derivatives compound. SDS of cas: 86847-84-9

Intermediate 6:[0121] A solution of intermediate 5 (19.28 g, 90.6 mmol) in THF (181 mL) was treated with 77-BuLi (108.8 mL, 272 mmol) and the resulting mixture was stirred at -20C for 3 h. After addition of DMF (20.81 mL, 271.86 mmol), the reaction was allowed to warm to rt. The reaction was poured into cold 6N HC1 and stirred for 15 min. The mixture was then neutralized with anhydrous K2C03 to pH=7 and extracted with Et20. The combined organic layers were washed with water, brine, dried over anhydrous Na2SC>4, concentrated in vacuo and purified by recrystallization from EtOAc and hexanes to afford N-(6-chloro-3-formylpyridin-2-yl)pivalamide (intermediate 6) (12.84 g, 59%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,86847-84-9, N-(6-Chloropyridin-2-yl)pivalamide, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; JIN, Jian; ROTH, Bryan; FRYE, Stephen; WO2012/3418; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 727356-19-6 ,Some common heterocyclic compound, 727356-19-6, molecular formula is C6H5BrClN, 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): 2-Bromo-6-(2,2-dipyridin-2-yl)propyl)pyridine 40 ml (100 mmol) of n-butyllithium (2.5 M in hexane) are added dropwise to a solution, cooled to -78 C., of 18.4 g (100 mmol) of 2,2′-ethylidenebis-pyridine [29280-41-9] in 500 ml of THF, and the mixture is stirred for a further 30 min. A solution of 20.6 g (100 mmol) of 2-bromo-6-chloromethylpyridine [727356-19-6] in 100 ml of THF is then added dropwise, and the mixture is then stirred at -78 C. for a further 15 min. After warming to room temperature, the solvent is removed in vacuo, the residue is taken up in 300 ml of dichloromethane, and the organic phase is washed twice with 100 ml of water each time and dried over magnesium sulfate. The residue is recrystallised twice from ethyl acetate/heptane. Yield: 19.5 g (55 mmol), 55%, 95.0% pure according to 1H-NMR.

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. 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; US2012/286254; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 105252-99-1, 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.105252-99-1, name is 4-Amino-6-fluoropyridin-2(1H)-one, molecular formula is C5H5FN2O, molecular weight is 128.1, as common compound, the synthetic route is as follows.

Step a: To a 0 C solution of 4-amino-6-fluoropyridin-2(1H)-one (490 mg, 3.83 mmol) in AcOH (19 mL) was added NIS (818 mg, 3.63 mmol). The reaction mixture solidated, was allowed to warm to RT, and stirred for 1 h. The volatiles were removed under reduced pressure. The residue was transferred to a separation funnel containing sat. aq. Na25203 (15 mL), sat. aq. NH4C1 (15 mL), and water (15 mL). The mixture was extracted with Et20 (4 x 50 mL) and the combined organic extracts were dried over Mg504, filtered, and the volatiles were removed under reduced pressure. The residue was purified by silica chromatography (0 to 5% gradient of MeOH/DCM) to give 4-amino-6-fluoro-3-iodopyridin-2(1H)-one (54 mg, 0.2 13 mmol) as a white solid. MS m/z 255.0 (M+H).

The chemical industry reduces the impact on the environment during synthesis 105252-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; CHEN, Zhuoliang; FORTANET, Jorge Farcia; LAMARCHE, Matthew J.; SENDZIK, Martin; TAMEZ, JR., Victoriano; YU, Bing; (237 pag.)WO2016/203405; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 107867-51-6, 5-(Trifluoromethyl)pyridine-2,3-diamine, 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, Formula: C6H6F3N3, blongs to pyridine-derivatives compound. Formula: C6H6F3N3

To a solution of l-(5-(3-bromobenzamido)pyridin-2-yl)cyclobutanecarboxylic acid (100 mg, 0.267 mmol) in pyridine (5 mL) was added 5-(trifluoromethyl)pyridine-2,3- diamine (48 mg, 0.27 mmol) and EDC (153 mg, 0.800 mmol) at RT. After the addition was complete, the reaction mixture was stirred at 30 C for 2 h. The reaction was cooled to RT, diluted with water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04i filtered and concentrated in vacuo to afford the title compound, which was used directly in next step without further purification. MS (EI) m/z 534 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,107867-51-6, 5-(Trifluoromethyl)pyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; FRADERA, Xavier; HAN, Yongxin; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; WHITE, Catherine; YU, Wensheng; (89 pag.)WO2019/27856; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 51173-05-8, 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 51173-05-8, name is 5-Fluoro-2-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

In Step A, compound zzl’ (1.2 g, 0.01 mol) was dissolved in sulfuric acid (2.7 mL) at room temperature. Premixed fuming nitric acid (1 mL) and sulfuric acid was added dropwise at 5-10 C. to the solution of compound zzl’. The reaction mixture was then heated at 85 C. for 1 hour, then was cooled to room temperature and poured into ice (20 g). The yellow solid precipitate was collected by filtration, washed with water and air dried to provide 1.01 g of compound zz2′.

According to the analysis of related databases, 51173-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-35-3, Adding some certain compound to certain chemical reactions, such as: 884494-35-3, name is 2-Chloro-5-fluoropyridin-3-ol,molecular formula is C5H3ClFNO, 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 884494-35-3.

Preparation 222 2-chloro-5-fluoro-3-methoxypyridine 2-chloro-5-fluoro-3-methoxypyridine (1.8 g, 72%) was prepared in an analogous manner to Preparation 153 using 2-chloro-5-fluoropyridin-3-ol (2.3 g, 16 mmol) and methanol (5 g, 156 mmol). 1H NMR (CDCl3, 400 MHz): delta 7.89 (d, J=2.70 Hz, 1H), 7.00 (dd, J=2.5, 9.1 Hz, 1H), 3.93 (s, 3H).

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. 884494-35-3, 2-Chloro-5-fluoropyridin-3-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; Strohbach, Joseph Walter; Akama, Tsutomu; Blakemore, David Clive; Jacobs, Robert Toms; Jones, Peter; Limburg, David Christopher; Oderinde, Martins Sunday; Perry, Matthew Alexander; Plattner, Jacob John; Torella, Rubben Federico; Zhou, Yasheen; Yeoh, Thean Yeow; (200 pag.)US2020/108083; (2020); 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 1159812-31-3, name is 7-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1159812-31-3

To 7-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine (2.14 g, 10.09 mmolAnd benzophenone imine (2.75g, 15.17mmol)In a solution of 1,4-dioxane (40 mL),Add Pd2(dba)3 (467.0 mg, 0.51 mmol),BINAP (95%, 664.4 mg, 1.01 mmol)And t-BuONa (1.94 g, 20.19 mmol).The reaction system was stirred at 100 C overnight.It was then cooled to room temperature and concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (MeOH / DCThe title compound was obtained as a yellow solid (2.56 g, yield: 81.2%).

With the rapid development of chemical substances, we look forward to future research findings about 1159812-31-3.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1147422-00-1 ,Some common heterocyclic compound, 1147422-00-1, molecular formula is C12H22N2O2, 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.

1-Methyloctahydro-1H-pyrrolo[3,2-c]pyridine To a solution of tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1.05 g, 4.64 mmol, Shah, S. K et. al, Bioorg. Med. Chem. Lett. 2005, 15, 977-982) in DCM (20 mL) was added TEA (1.29 mL, 9.29 mmol) followed by dropwise addition of benzyl chloroformate (0.795 mL, 5.57 mmol) at ambient temperature. After about 4 h, the mixture was diluted with DCM and then washed with water and brine. The organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with a gradient of 0-75% EtOAc in heptane to give 5-benzyl 1-tert-butyl hexahydro-1H-pyrrolo[3,2-c]pyridine-1,5(6H)-dicarboxylate (1.05 g, 63% yield): LC/MS (Table 1, Method a) Rt=2.59 min; MS m/z: 361 (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. 1147422-00-1, tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; US2011/152243; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 139585-48-1, Adding some certain compound to certain chemical reactions, such as: 139585-48-1, name is 2-Chloro-5-methoxypyridine,molecular formula is C6H6ClNO, 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 139585-48-1.

(Step 3) Preparation of methyl 2-[(2-methoxyethoxy)methoxy]-3-(5-methoxypyridin-2-ylamino)benzoate To a solution of 3-amino-2-((2-methoxyethoxy)methoxy)benzoic acid methyl ester 1.25 g (4.9 mmol) of step 2 in 1,4-dioxane 10 mL were added 2-chloro-5-methoxypyridine 0.70 g (4.9 mmol), Pd(OAc)2 0.11 g (0.49 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 0.31 g (0.49 mmol) and Cs2CO3 3.85 g (9.8 mmol), followed by stirring at 90 C. for 12 hrs. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, diluted with ethylacetate, and washed with a saturated sodium bicarbonate solution and a saturated NaCl solution. After drying over magnesium sulfate and concentration in a vacuum, purification by column chromatography (developing solvent: ethylacetate/hexane=1/2) afforded 1.2 g of the title compound (yield 68%).

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. 139585-48-1, 2-Chloro-5-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Daewoong Pharmaceutical Co., Ltd.; US8026235; (2011); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 169280-83-5, tert-Butyl (5-(hydroxymethyl)pyridin-2-yl)carbamate, 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 C11H16N2O3, blongs to pyridine-derivatives compound. Computed Properties of C11H16N2O3

Production Example 1 To a mixture of tert-butyl [5-(hydroxymethyl)pyridine-2-yl]carbamate (2.13 g), triethylamine (5.3 ml), and DMSO (15 ml), a sulfur trioxide-pyridine complex (3.02 g) in a DMSO solution (15 ml) was added dropwise, followed by stirring at room temperature for 4.5 hours. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After removing the desiccant, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 2.00 g of tert-butyl (5-formylpyridin-2-yl)carbamate.

The synthetic route of 169280-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; EP2216330; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem