Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 960289-03-6, 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, 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, name: 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, blongs to pyridine-derivatives compound. name: 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one

Preparation 10; 2-(4-Fluoro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridine-7-one; Add tetrakis(triphenylphosphine) palladium(O) (0.075g, 0.065 mmol) to a degassed solution of 2-bromo-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (0.5 g, 2.15 mmol), 4-fluorophenylboronic acid (0.30 g, 2.15 mmol), and sodium carbonate (0.46 g, 4.30 mmol) in N,N-dimethylformamide (21 mL), methanol (5 mL) and water (1 mL). Heat the reaction at 90 0C for 16 h. Allow the reaction to cool to RT and pour into water (75 mL). Filter the resulting solid and dry in vacuo at 80 0C to give 0.40 g (75%) of the title compound. MS/ES m/z 248.0 [M+H]+ .

The synthetic route of 960289-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146759; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 82090-52-6, Adding some certain compound to certain chemical reactions, such as: 82090-52-6, name is Imidazo[1,2-a]pyridin-2-ylmethanol,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 82090-52-6.

Example 21; N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(imidazo[1,2-a]pyridin-2- ylmethoxy) pyrimidine-5-carboxamide A mixture of N- {5-[(cyclopropylanaino) carbonyl]-2-methylphenyl}-2- (methylsulfonyl) pyrimidine-5-carboxamide (120mg, 0. 32mmol), imidazo [1, 2-a] pyridine-2- methanol (48mg, 0. 32mmol) and potassium carbonate (44mg, 0. 32mmol) in THF (5mL) was heated to 67C for 3.5 h. The mixture was cooled to room temperature and partitioned between DCM and water and the layers separated. The aqueous layer was extracted with DCM and the combined organic extracts dried (Mg04), filtered and concentrated at reduced pressure to give a yellow oil. This material was purified by silica column chromatography, eluting with a gradient of 0 to 8% methanol in DCM to give the title compound as a white solid (33 mg, 23%); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.67 (m, 2H), 2.27 (s, 3H), 2. 83 (m, 1H), 5.70 (s, 2H), 7.26 (t, 1H), 7.35 (d, 1H), 7.66 (m, 2H), 7.78 (d, 1H), 7. 83 (d, 1H), 8.30 (s, 1H), 8. 38 (d, 1H), 8. 75 (d, 1 H), 9. 17 (s, 2H), 10.16 (s, 1H) ; Mass Spectrum : M-H- 441, M+H+ 443.

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. 82090-52-6, Imidazo[1,2-a]pyridin-2-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/61465; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1256811-02-5, 1-(5-Bromo-2-methoxypyridin-3-yl)ethanone, 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, HPLC of Formula: C8H8BrNO2, blongs to pyridine-derivatives compound. HPLC of Formula: C8H8BrNO2

[0118] 1-(5-Bromo-2-methoxy-pyridin-3-yl)ethanone (XXXVI) (200 mg, 1.404mmol) was dissolved in N,N-dimethylformamidedimethyl acetal (DMFDMA) (1.7 ml, 14.03 mmol), and the resulting solution was stirred with reflux for 24 hrs.The solution was cooled and evaporated and concentrated under reduced pressure to give a yellow solid. The solid wasdissolved in methanol (MeOH) (1 mL) and 25 % sodium methoxide (NaOMe) (186 mL, 6.212 mmol) and guanidinhydrochloride (498.0 mg, 6.212 mmol) were added dropwise to the resulting solution. And then, the solution was stirredwith reflux for 24 hrs and cooled. The solution was diluted with ethylacetate (EA) and washed with water, and the organicsolvent was dried over anhydrous magnesium sulfate (MgSO4), filtered, and evaporated and concentrated under reducedpressure to give the title compound (20.3 mg, 55 %).1H NMR (400 MHz, CDCl3) delta 8.50 (s, 1H), 8.43 (s, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.35 (d, J = 7.6 Hz, 1H), 4.07 (s, 3H).

The synthetic route of 1256811-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 29241-65-4, 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. 29241-65-4, name is 5-Bromo-2-chloronicotinic acid, molecular formula is C6H3BrClNO2, 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.

Compounds are represented in generic form, with sub stituents as noted in compound descriptions elsewhere herein. A more specific example is set forth below. In one aspect, ethers of type 6.7 can be prepared beginning with the commercially available 5-bromo-2-chloronicotinic acid, which is converted to the corresponding ester by reaction with methanol in the presence of an acid such as hydrochloric acid to yield compound 6.2. Alkylation to provide compound 6.3 is accomplished by use of a Suzuki cross coupling reaction using potassium allyltrifluoroborate in the presence of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II). Reaction with 4-methoxybenzylamine affords compound 6.4. A cross-coupling reaction between compound 6.4 and benzyl alcohol in the presence of CuI, Cs2CO3, and a diamine ligand yields the aryl ether, compound 6.5. The p-methoxybenzyl protecting group is removed using cerium(IV) ammonium nitrate (CAN), followed by reduction of the carbonyl using lithium aluminum hydride. The amide, compound 6.7, is formed by reaction of the 3-(benzyloxy)-5,6,7,8-tetrahydro-1,6-naphthyridine, formed in the previous step, with benzoyl chloride.

According to the analysis of related databases, 29241-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Conn, P. Jeffrey; Lindsley, Craig W.; Stauffer, Shaun R.; Manka, Jason; Jacobs, Jon; Zhou, Ya; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Dawson, Eric S.; US2012/178776; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, molecular formula is C7H5ClN2, molecular weight is 152.58, as common compound, the synthetic route is as follows.Quality Control of 6-(Chloromethyl)-2-cyanopyridine

Reference Example 149-1 tert-Butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-3-methyl-2-oxobutyl]-5-methoxyphenyl}carbamate Under an argon atmosphere, to a solution of tert-butyl [5-methoxy-2-(3-methyl-2-oxobutyl)phenyl]carbamate (337 mg) in N,N-dimethylformamide (4 mL) was added sodium hydride (50-72% in oil, 56 mg) under ice-cooling, and the mixture was stirred for 30 minutes. 6-(Chloromethyl)pyridine-2-carbonitrile (167 mg) was added thereto, followed by stirring for 1 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (271 mg). 1H-NMR (CDCl3) delta ppm: 0.91 (3H, d, J=6.5 Hz), 1.07 (3H, d, J=7.3 Hz), 1.57 (9H, s), 2.56-2.72 (1H, m), 3.18 (1H, dd, J=8.2, 15.9 Hz), 3.61 (1H, dd, J=6.8, 15.9 Hz), 3.77 (3H, s), 4.65-4.74 (1H, m), 6.58 (1H, dd, J=2.8, 8.7 Hz), 6.92 (1H, d, J=8.7 Hz), 7.22-7.29 (1H, m), 7.35 (1H, d, J=2.8 Hz), 7.46-7.60 (2H, m), 7.65 (1H, t, J=7.8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Tatani, Kazuya; Kondo, Atsushi; Kondo, Tatsuhiro; Kawamura, Naohiro; Seto, Shigeki; Kohno, Yasushi; US2013/317065; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 161117-83-5, 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 161117-83-5 as follows.

Under a nitrogen atmosphere, a whole batch of compound II in tetrahydrofuran solution, 93.6 g of tetramethylethylenediamine (0.8 mol, 2.0 eq) was added to the reaction flask.Cool to -78 , add 261.1g n-butyl lithium n-hexane solution (0.96mol, 2.4eq) dropwise,After the dropwise addition, the reaction was kept for 2 hours.After the heat preservation is completed, the temperature is controlled to -40 C, 58.9 g of N-N-dimethylformamide (0.8 mol, 2.0 eq) is added, and the mixture is stirred for 30 min.After the reaction is completed, the temperature is controlled at 0-20 C, the pH value is adjusted to 5-7 with 3N hydrochloric acid, the layers are separated, 200g of methylene chloride is added to the aqueous phase, and extraction is performed once.Combine the organic phases, concentrate under reduced pressure until a large amount of solid precipitates, add 300g of n-heptane and steam to a certain volume.Beating and filtering to obtain 79.3g of yellow solid (78% yield in two steps) is compound III.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,161117-83-5, its application will become more common.

Reference:
Patent; Cheng Da Pharmaceutical Co., Ltd.; Shi Yuhua; Qian Wei; Feng Yu; Huang Xing; Dang Junkui; Wang Zhipeng; Dong Changming; Xu Hong; Huang Zongxi; Chen Ye; Shen Huafei; Zhang Jun; (12 pag.)CN110964011; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 386704-05-8, 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 386704-05-8, name is 2-Chloro-6-(trifluoromethyl)nicotinamide. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 6 Preparation of 3-amino-2-chloro-6-trifluoromethylpyridine To a mixture of 200 g of 2-chloro-6-trifluoromethylnicotinamide and 1,000 ml of water, 432 ml of a 11.6 wt% aqueous sodium hypochlorite solution and 190 ml of a 10 N aqueous sodium hydroxide solution were dropwise added in order under cooling with ice, followed by stirring at 90C for 30 minutes. The reaction mixture was cooled to 10C, crystals precipitated were collected by filtration, washed three times with 100 ml of cooled water, and then dried at room temperature for 24 hours to obtain 144 g of 3-amino-2-chloro-6-trifluoromethylpyridine (melting point: 96 to 97C). 1H-NMR(CDCl3) delta= 4.47(2H, bs, NH2), 7.09(1H, d, J= 7.8 Hz), 7.42(1H, d, J= 7.8 Hz).

According to the analysis of related databases, 386704-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP2251329; (2010); 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. 98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Hydroxymethyl)-4-nitropyridine

A 200-mL round-bottomed flask was charged with n-butanol (50 mL) and NaH (2.12 g, 53.57 mmol) and stirred at 0 C under inert atmosphere for 1 h. After, (4~nitropyndin-2~yl)methanol (1.0 g, 6.5 mmol) was added to the stirring reaction mixture. The resulting reaction mixture was refluxed for 20 h. After this period, the reaction mixture was cooled with an ice bath, quenched with saturated aqueous NFUC and concentrated in vacuo. The resulting reside was extracted with EtOAc (3 c 75 mL). The combined organic layers were dried over anhydrous Na2S04, filtered, and concentrated in vacuo. The crude material purified by flash chromatography (80 to 100% EtOAc in hexanes) on silica gel (55 mL) to afford (4- butoxypyridin-2-yl)methanol (599 mg, 51 % yield) as a brown oil.

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, 98197-88-7, 2-(Hydroxymethyl)-4-nitropyridine.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; KOIDE, Kazunori; BEIN, Kiflai; BRESSIN, Robert, Kruger; BURROWS, James, Proviano; GAMBINO, Adriana; LEIKAUF, George, D.; PHAM, Dianne; (80 pag.)WO2020/27905; (2020); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1034467-27-0 , The common heterocyclic compound, 1034467-27-0, name is 2-Fluoro-4-iodo-5-(methoxymethoxy)pyridine, molecular formula is C7H7FINO2, 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 19; 6-Fluoro-4-iodo-pyridin-3 -ol; Add HCl (3 M in water, 31 mL, 93.01 mmol) to a solution of 2-fluoro-4-iodo-5- methoxymethoxy-pyridine (3.9 g, 13.78 mmol) in THF (20 mL). Stir the mixture at 60 0C for 3 hours. Cool down the mixture. Adjust the pH to 7 with slow addition of saturated aqueous sodium bicarbonate solution. Extract the solution with ethyl acetate three times. Wash the organic layer with saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to afford the title compound (3.2 g, 97.18 %) as a yellow solid. MS (EI) m/z 240 [M+l]+.

The synthetic route of 1034467-27-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/76705; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59105-50-9, 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.59105-50-9, name is (5-Bromopyridin-3-yl)(phenyl)methanone, molecular formula is C12H8BrNO, molecular weight is 262.1, as common compound, the synthetic route is as follows.

The 3-bromo-5-benzoyl-pyridine (270 mg, 1 . 0mmol), potassium thioacetic acid (183 mg, 1 . 61mmol) dissolved in dioxane (10 ml), add DIPEA (0.36 ml, 2 . 1mmol), after the replacement Ar gas, adding Pd2(dba)3, (23.8 mg, 0 . 026mmol), Xantphos (30 mg, 0 . 052mmol), Ar gas replacement again 3 times, the temperature is increased to 100 C reflux reaction 10h.The filtrate was washed with ethyl acetate, combined with ethyl acetate and filtrate, evaporated to dryness and the residue was purified by silica gel column chromatography to give an orange-red oil (116 mg, 45%).

Statistics shows that 59105-50-9 is playing an increasingly important role. we look forward to future research findings about (5-Bromopyridin-3-yl)(phenyl)methanone.

Reference:
Patent; Chinese Academy of Sciences, Shanghai Institute of Materia Medica; Nanjing Changao Pharmaceutical Technology Co., LTD; YANG, YU SHE; LING, CHEN YU; FU, LI QIANG; LI, ZHAN; (49 pag.)CN103626693; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem